WO2019117571A1 - Organic compound and organic electroluminescent device comprising same - Google Patents
Organic compound and organic electroluminescent device comprising same Download PDFInfo
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- WO2019117571A1 WO2019117571A1 PCT/KR2018/015641 KR2018015641W WO2019117571A1 WO 2019117571 A1 WO2019117571 A1 WO 2019117571A1 KR 2018015641 W KR2018015641 W KR 2018015641W WO 2019117571 A1 WO2019117571 A1 WO 2019117571A1
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- Prior art keywords
- group
- aryl
- alkyl
- compound
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- 150000002894 organic compounds Chemical class 0.000 title abstract description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 97
- 239000010410 layer Substances 0.000 claims description 111
- -1 alkyl boron Chemical compound 0.000 claims description 74
- 125000003118 aryl group Chemical group 0.000 claims description 73
- 238000000034 method Methods 0.000 claims description 68
- 125000004429 atom Chemical group 0.000 claims description 51
- 125000000217 alkyl group Chemical group 0.000 claims description 48
- 125000001072 heteroaryl group Chemical group 0.000 claims description 41
- 125000001424 substituent group Chemical group 0.000 claims description 39
- 125000003342 alkenyl group Chemical group 0.000 claims description 22
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- 125000004104 aryloxy group Chemical group 0.000 claims description 20
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 20
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 20
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 19
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 19
- 125000001624 naphthyl group Chemical group 0.000 claims description 19
- 239000012044 organic layer Substances 0.000 claims description 19
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 18
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 18
- 125000000304 alkynyl group Chemical group 0.000 claims description 17
- 125000004076 pyridyl group Chemical group 0.000 claims description 17
- 238000002347 injection Methods 0.000 claims description 14
- 239000007924 injection Substances 0.000 claims description 14
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 125000005647 linker group Chemical group 0.000 claims description 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 13
- 239000011368 organic material Substances 0.000 claims description 13
- 125000005104 aryl silyl group Chemical group 0.000 claims description 12
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 11
- 239000008280 blood Substances 0.000 claims description 11
- 210000004369 blood Anatomy 0.000 claims description 11
- GKTNLYAAZKKMTQ-UHFFFAOYSA-N n-[bis(dimethylamino)phosphinimyl]-n-methylmethanamine Chemical group CN(C)P(=N)(N(C)C)N(C)C GKTNLYAAZKKMTQ-UHFFFAOYSA-N 0.000 claims description 11
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 11
- 150000004982 aromatic amines Chemical class 0.000 claims description 10
- 125000000732 arylene group Chemical group 0.000 claims description 9
- 125000005549 heteroarylene group Chemical group 0.000 claims description 9
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 9
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 8
- 125000005264 aryl amine group Chemical group 0.000 claims description 8
- 229910052805 deuterium Inorganic materials 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 7
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 6
- 229910052796 boron Inorganic materials 0.000 claims description 6
- 230000005525 hole transport Effects 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 238000006467 substitution reaction Methods 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 4
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 238000002360 preparation method Methods 0.000 description 102
- 230000015572 biosynthetic process Effects 0.000 description 84
- 238000003786 synthesis reaction Methods 0.000 description 84
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 51
- 239000000463 material Substances 0.000 description 45
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 28
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 21
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 13
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 13
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 13
- 230000032258 transport Effects 0.000 description 13
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 12
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 125000006267 biphenyl group Chemical group 0.000 description 10
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 10
- 239000000376 reactant Substances 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 9
- 239000002019 doping agent Substances 0.000 description 8
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 125000004306 triazinyl group Chemical group 0.000 description 8
- 235000010290 biphenyl Nutrition 0.000 description 7
- 239000007795 chemical reaction product Substances 0.000 description 7
- 239000012153 distilled water Substances 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 229940125898 compound 5 Drugs 0.000 description 5
- 125000004494 ethyl ester group Chemical group 0.000 description 5
- LENLQGBLVGGAMF-UHFFFAOYSA-N tributyl([1,2,4]triazolo[1,5-a]pyridin-6-yl)stannane Chemical compound C1=C([Sn](CCCC)(CCCC)CCCC)C=CC2=NC=NN21 LENLQGBLVGGAMF-UHFFFAOYSA-N 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- MJUSCWWLVUDRHT-UHFFFAOYSA-N 2-bromo-[1,2,4]triazolo[1,5-a]pyridine Chemical compound C1=CC=CN2N=C(Br)N=C21 MJUSCWWLVUDRHT-UHFFFAOYSA-N 0.000 description 4
- 0 CC*(C)N=CC Chemical compound CC*(C)N=CC 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- MAQCYJPBTCDJPZ-UHFFFAOYSA-N [4-(6-chloronaphthalen-2-yl)phenyl]boronic acid Chemical compound ClC=1C=C2C=CC(=CC2=CC1)C1=CC=C(C=C1)B(O)O MAQCYJPBTCDJPZ-UHFFFAOYSA-N 0.000 description 4
- 229940125782 compound 2 Drugs 0.000 description 4
- 238000005401 electroluminescence Methods 0.000 description 4
- 125000006575 electron-withdrawing group Chemical group 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 239000008213 purified water Substances 0.000 description 4
- GRPJWMIQQFQDEZ-UHFFFAOYSA-N 2-[4-(4-chloronaphthalen-1-yl)phenyl]-[1,2,4]triazolo[1,5-a]pyridine Chemical compound ClC1=CC=C(C2=CC=CC=C12)C1=CC=C(C=C1)C1=NN2C(C=CC=C2)=N1 GRPJWMIQQFQDEZ-UHFFFAOYSA-N 0.000 description 3
- MRBGXZFYURRILS-UHFFFAOYSA-N 2-[4-(5-chloronaphthalen-1-yl)phenyl]-[1,2,4]triazolo[1,5-a]pyridine Chemical compound ClC1=C2C=CC=C(C2=CC=C1)C1=CC=C(C=C1)C1=NN2C(C=CC=C2)=N1 MRBGXZFYURRILS-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- NPEIEHDNSFUKLS-UHFFFAOYSA-N [3-(5-chloronaphthalen-1-yl)phenyl]boronic acid Chemical compound ClC1=C2C=CC=C(C2=CC=C1)C=1C=C(C=CC1)B(O)O NPEIEHDNSFUKLS-UHFFFAOYSA-N 0.000 description 3
- MOSQGJRJTFDBEC-UHFFFAOYSA-N [3-(7-chloronaphthalen-2-yl)phenyl]boronic acid Chemical compound ClC1=CC=C2C=CC(=CC2=C1)C=1C=C(C=CC1)B(O)O MOSQGJRJTFDBEC-UHFFFAOYSA-N 0.000 description 3
- JTEJPGFKQWEFPJ-UHFFFAOYSA-N [4-(4-chloronaphthalen-1-yl)phenyl]boronic acid Chemical compound ClC1=CC=C(C2=CC=CC=C12)C1=CC=C(C=C1)B(O)O JTEJPGFKQWEFPJ-UHFFFAOYSA-N 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- 125000003454 indenyl group Chemical class C1(C=CC2=CC=CC=C12)* 0.000 description 3
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
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- 229910052711 selenium Inorganic materials 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
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- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 2
- WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 description 2
- UDQTXCHQKHIQMH-KYGLGHNPSA-N (3ar,5s,6s,7r,7ar)-5-(difluoromethyl)-2-(ethylamino)-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazole-6,7-diol Chemical compound S1C(NCC)=N[C@H]2[C@@H]1O[C@H](C(F)F)[C@@H](O)[C@@H]2O UDQTXCHQKHIQMH-KYGLGHNPSA-N 0.000 description 2
- HUWSZNZAROKDRZ-RRLWZMAJSA-N (3r,4r)-3-azaniumyl-5-[[(2s,3r)-1-[(2s)-2,3-dicarboxypyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]amino]-5-oxo-4-sulfanylpentane-1-sulfonate Chemical compound OS(=O)(=O)CC[C@@H](N)[C@@H](S)C(=O)N[C@@H]([C@H](C)CC)C(=O)N1CCC(C(O)=O)[C@H]1C(O)=O HUWSZNZAROKDRZ-RRLWZMAJSA-N 0.000 description 2
- DEVSOMFAQLZNKR-RJRFIUFISA-N (z)-3-[3-[3,5-bis(trifluoromethyl)phenyl]-1,2,4-triazol-1-yl]-n'-pyrazin-2-ylprop-2-enehydrazide Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C2=NN(\C=C/C(=O)NNC=3N=CC=NC=3)C=N2)=C1 DEVSOMFAQLZNKR-RJRFIUFISA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- LMMOORYPTYHMOP-UHFFFAOYSA-N 2-[4-(6-chloronaphthalen-2-yl)phenyl]-6,8-diphenyl-[1,2,4]triazolo[1,5-a]pyridine Chemical compound C1=CC=C(C=C1)C2=CC(=CN3C2=NC(=N3)C4=CC=C(C=C4)C5=CC6=C(C=C5)C=C(C=C6)Cl)C7=CC=CC=C7 LMMOORYPTYHMOP-UHFFFAOYSA-N 0.000 description 2
- VVCMGAUPZIKYTH-VGHSCWAPSA-N 2-acetyloxybenzoic acid;[(2s,3r)-4-(dimethylamino)-3-methyl-1,2-diphenylbutan-2-yl] propanoate;1,3,7-trimethylpurine-2,6-dione Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O.CN1C(=O)N(C)C(=O)C2=C1N=CN2C.C([C@](OC(=O)CC)([C@H](C)CN(C)C)C=1C=CC=CC=1)C1=CC=CC=C1 VVCMGAUPZIKYTH-VGHSCWAPSA-N 0.000 description 2
- NPRYCHLHHVWLQZ-TURQNECASA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynylpurin-8-one Chemical compound NC1=NC=C2N(C(N(C2=N1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C NPRYCHLHHVWLQZ-TURQNECASA-N 0.000 description 2
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 2
- XOJXLAMKKYFLAH-UHFFFAOYSA-N 2-bromo-6,8-diphenyl-[1,2,4]triazolo[1,5-a]pyridine Chemical compound BrC1=NN2C(C(=CC(=C2)C2=CC=CC=C2)C2=CC=CC=C2)=N1 XOJXLAMKKYFLAH-UHFFFAOYSA-N 0.000 description 2
- IKSNGEACZZVWSC-UHFFFAOYSA-N 2-bromo-8-phenyl-[1,2,4]triazolo[1,5-a]pyridine Chemical compound C=1C=CN2N=C(Br)N=C2C=1C1=CC=CC=C1 IKSNGEACZZVWSC-UHFFFAOYSA-N 0.000 description 2
- DFRAKBCRUYUFNT-UHFFFAOYSA-N 3,8-dicyclohexyl-2,4,7,9-tetrahydro-[1,3]oxazino[5,6-h][1,3]benzoxazine Chemical compound C1CCCCC1N1CC(C=CC2=C3OCN(C2)C2CCCCC2)=C3OC1 DFRAKBCRUYUFNT-UHFFFAOYSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- XFJBGINZIMNZBW-CRAIPNDOSA-N 5-chloro-2-[4-[(1r,2s)-2-[2-(5-methylsulfonylpyridin-2-yl)oxyethyl]cyclopropyl]piperidin-1-yl]pyrimidine Chemical compound N1=CC(S(=O)(=O)C)=CC=C1OCC[C@H]1[C@@H](C2CCN(CC2)C=2N=CC(Cl)=CN=2)C1 XFJBGINZIMNZBW-CRAIPNDOSA-N 0.000 description 2
- HCCNBKFJYUWLEX-UHFFFAOYSA-N 7-(6-methoxypyridin-3-yl)-1-(2-propoxyethyl)-3-(pyrazin-2-ylmethylamino)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C=NC(OC)=CC=3)=NC=C2N=C1NCC1=CN=CC=N1 HCCNBKFJYUWLEX-UHFFFAOYSA-N 0.000 description 2
- SUFKKFLJJMKVJJ-UHFFFAOYSA-N 8-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-amine Chemical compound BrC1=CC=CN2N=C(N)N=C21 SUFKKFLJJMKVJJ-UHFFFAOYSA-N 0.000 description 2
- IRBAWVGZNJIROV-SFHVURJKSA-N 9-(2-cyclopropylethynyl)-2-[[(2s)-1,4-dioxan-2-yl]methoxy]-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(C#CC4CC4)C=C3CCN2C(=O)N=C1OC[C@@H]1COCCO1 IRBAWVGZNJIROV-SFHVURJKSA-N 0.000 description 2
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- JXAOGZHPRWTDSJ-UHFFFAOYSA-N [4-(5-chloronaphthalen-1-yl)phenyl]boronic acid Chemical compound ClC1=C2C=CC=C(C2=CC=C1)C1=CC=C(C=C1)B(O)O JXAOGZHPRWTDSJ-UHFFFAOYSA-N 0.000 description 2
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Images
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
Definitions
- the present invention relates to a novel organic compound that can be used as a material for an organic electroluminescence device and an organic electroluminescence device including the same.
- the organic electroluminescent device when a voltage is applied between two electrodes, holes are injected into the organic layer in the anode, and electrons are injected into the organic layer in the cathode. When the injected holes and electrons meet, an exciton is formed. When the exciton falls to the ground state, light is emitted. At this time, the material used as the organic material layer can be classified into a light emitting material, a hole injecting material, a hole transporting material, an electron transporting material, an electron injecting material and the like depending on its function.
- the luminescent material can be classified into blue, green and red luminescent materials according to luminescent colors and yellow and orange luminescent materials to realize better natural colors. Further, in order to increase the color purity and increase the luminous efficiency through energy transfer, a host / dopant system can be used as a light emitting material.
- the dopant material can be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt.
- a metal complex compound containing heavy atoms such as Ir and Pt.
- NPB, BCP and Alq 3 have been widely known as the hole injecting layer, the hole transporting layer, the hole blocking layer and the electron transporting layer material, and anthracene derivatives have been reported as the light emitting layer material.
- metal complex compounds containing Ir such as Firpic, Ir (ppy) 3 , (acac) Ir (btp) 2 and the like having advantages in terms of efficiency improvement of the light emitting layer material are blue, green, 4,4-dicarbazolybiphenyl (CBP) is used as a phosphorescent dopant material for red phosphorescent dopants.
- n is an integer from 1 to 3;
- Z 1 to Z 3 are each independently N or C (R 3 ), and one is necessarily N;
- L 1 and L 3 are each independently selected from the group consisting of a single bond, a C 6 to C 18 arylene group and a heteroarylene group having 5 to 18 nucleus atoms;
- L 2 is an arylene group having 6 to 18 carbon atoms or a heteroarylene group having 5 to 18 nuclear atoms;
- R 1 to R 3 are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ of C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C 1 ⁇ alkyloxy group of C 40, C 6 ⁇ aryloxy group of C 60, C 3 ⁇ C 40 alkylsilyl group, C group 6 ⁇ C 60 aryl silyl, C 1 ⁇ arylboronic of C 40 group of an alkyl boron, C 6 ⁇ C 60 group, C 6 ⁇ C 60 aryl phosphazene group, is selected from the group consisting of an aryl amine of the C 6 ⁇ C 60
- Ar 1 and Ar 2 are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ of C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C 1 ⁇ alkyloxy group of C 40, C 6 ⁇ aryloxy group of C 60, C 3 ⁇ C 40 alkylsilyl group, C group 6 ⁇ C 60 aryl silyl, C 1 ⁇ arylboronic of C 40 group of an alkyl boron, C 6 ⁇ C 60 group, C 6 ⁇ C 60 aryl phosphazene group, C 6 ⁇ C 60 mono or diaryl phosphine blood group and a C 6
- Ar 1 , Ar 2, and Ar 3 which are the above-mentioned L 1 to L 3 arylene group and heteroarylene group
- the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkylboron group, arylboron group of R 1 to R 3 A halogen atom, a cyano group, a nitro group, a C 1 to C 40 alkyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkenyl group, a substituted or unsubstituted aryl group, ⁇ C 40 of the alkynyl group, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 aryl
- the present invention provides an organic electroluminescent device including a cathode, a cathode, and at least one organic layer interposed between the anode and the cathode, wherein at least one of the organic layers includes one or more compounds represented by Formula 1 .
- Alkyl in the present invention is a monovalent substituent derived from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms, and examples thereof include methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl And the like, but are not limited thereto.
- alkenyl " is a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon double bond. Examples thereof include vinyl, But are not limited to, allyl, isopropenyl, 2-butenyl, and the like.
- " alkynyl " in the present invention is a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon triple bond. Examples thereof include ethynyl, , 2-propynyl, and the like, but are not limited thereto.
- Aryl " in the present invention means a monovalent substituent derived from a C6-C60 aromatic hydrocarbon having a single ring or a combination of two or more rings. Further, it is preferable that two or more rings are condensed with each other and only carbon atoms are contained as the ring-forming atoms (for example, the number of carbon atoms may be from 8 to 60) and the whole molecule is a non-aromacity monovalent Substituents may also be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, fluorenyl, and the like.
- Heteroaryl in the present invention means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. Wherein one or more carbons, preferably one to three carbons, of the ring are substituted with a heteroatom selected from N, O, P, S and Se. In addition, it is preferable that two or more rings are pendant or condensed with each other, and include hetero atoms selected from N, O, P, S and Se besides carbon as a ring-forming atom, < / RTI > aromacity).
- heteroaryls include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; Such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl, and the like. ring; Imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.
- " aryloxy " means a monovalent substituent represented by RO-, and R represents aryl having 5 to 60 carbon atoms.
- R represents aryl having 5 to 60 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.
- " alkyloxy " in the present invention means a monovalent substituent group represented by R'O-, wherein R 'represents 1 to 40 alkyl, and may be linear, branched or cyclic . ≪ / RTI > Examples of such alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.
- Arylamine " in the present invention means an amine substituted with aryl having 6 to 60 carbon atoms.
- Cycloalkyl " in the present invention means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms.
- Examples of such cycloalkyls include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.
- Heterocycloalkyl " in the present invention means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, wherein at least one of the carbons, preferably one to three carbons, S or Se. ≪ / RTI > Examples of such heterocycloalkyls include, but are not limited to, morpholine, piperazine, and the like.
- Alkylsilyl " in the present invention is silyl substituted with alkyl having 1 to 40 carbon atoms, and " arylsilyl " means silyl substituted with aryl having 5 to 60 carbon atoms.
- condensed rings means condensed aliphatic rings, condensed aromatic rings, condensed heteroaliphatic rings, condensed heteroaromatic rings, or a combination thereof.
- the compound of the present invention is excellent in thermal stability, carrier transport ability, light emitting ability, and the like, it can be effectively applied as an organic material layer material of an organic electroluminescent device.
- the organic electroluminescent device including the compound of the present invention in the organic material layer can be effectively applied to a full color display panel, etc. in terms of light emitting performance, driving voltage, lifetime and efficiency.
- FIG. 1 is a cross-sectional view of an organic electroluminescent device according to an embodiment of the present invention.
- FIG. 2 is a cross-sectional view of an organic electroluminescent device according to an embodiment of the present invention.
- organic layer 31 hole transport layer
- Electron transport layer 35 Electron transport layer
- novel compounds of the present invention can be represented by the following formula
- n is an integer from 1 to 3;
- Z 1 to Z 3 are each independently N or C (R 3 ), and one is necessarily N;
- L 1 and L 3 are each independently selected from the group consisting of a single bond, a C 6 to C 18 arylene group and a heteroarylene group having 5 to 18 nucleus atoms;
- L 2 is an arylene group having 6 to 18 carbon atoms or a heteroarylene group having 5 to 18 nuclear atoms;
- R 1 to R 3 are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ of C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C 1 ⁇ alkyloxy group of C 40, C 6 ⁇ aryloxy group of C 60, C 3 ⁇ C 40 alkylsilyl group, C group 6 ⁇ C 60 aryl silyl, C 1 ⁇ arylboronic of C 40 group of an alkyl boron, C 6 ⁇ C 60 group, C 6 ⁇ C 60 aryl phosphazene group, is selected from the group consisting of an aryl amine of the C 6 ⁇ C 60
- Ar 1 and Ar 2 are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ of C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C 1 ⁇ alkyloxy group of C 40, C 6 ⁇ aryloxy group of C 60, C 3 ⁇ C 40 alkylsilyl group, C group 6 ⁇ C 60 aryl silyl, C 1 ⁇ arylboronic of C 40 group of an alkyl boron, C 6 ⁇ C 60 group, C 6 ⁇ C 60 aryl phosphazene group, C 6 ⁇ C 60 mono or diaryl phosphine blood group and a C 6
- Ar 1 , Ar 2, and Ar 3 which are the above-mentioned L 1 to L 3 arylene group and heteroarylene group
- the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkylboron group, arylboron group of R 1 to R 3 A halogen atom, a cyano group, a nitro group, a C 1 to C 40 alkyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkenyl group, a substituted or unsubstituted aryl group, ⁇ C 40 of the alkynyl group, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 aryl
- the compound represented by the formula (1) of the present invention has a basic skeleton by linking an indene derivative containing at least one nitrogen (N) and a phenylene group substituted by at least one cyano group through a linker.
- Compounds represented by formula (1) having such a structure are electrochemically stable, electron mobility is superior as well as high glass transition temperature and thermal stability as compared with conventionally known six-membered heterocyclic structures. Further, by introducing a cyano group, which is a functional group having a strong electron-attracting ability, two or more electron-withdrawing groups (EWG) can be provided to improve the electron transfer rate, so that it can have physicochemical properties more suitable for electron injection and electron transport layer .
- EWG electron-withdrawing groups
- the compound of the formula (1) of the present invention when used for an organic electroluminescent device, excellent thermal stability and carrier transport ability (in particular, electron transporting ability and light emitting ability) can be expected as well as driving voltage, Can be improved, and high triple-energetic energy can represent an excellent efficiency increase due to the triplet-triplet fusion (TTF) effect as the latest ETL material.
- TTF triplet-triplet fusion
- the compounds represented by formula (1) of the present invention can be produced by coupling a phenylene group substituted with one or more cyano groups, which is a functional group having strong electron-attracting ability, to an indene derivative containing at least one nitrogen (N) It shows the gap value and it is easy to control the HOMO and LUMO energy levels according to the direction or position of the substituent.
- the organic electroluminescent device using such a compound can exhibit a high electron transporting property.
- the compound represented by the general formula (1) of the present invention can be used as an organic layer material of an organic electroluminescence device, preferably a light emitting layer material (blue phosphorescent host material), an electron transporting layer / injection layer material emitting auxiliary layer material, More preferably, it can be used as a light emitting layer material, an electron transporting layer material, and an electron transporting layer material.
- the organic electroluminescent device including the compound of Formula 1 can be greatly improved in performance and lifetime, and the full-color organic luminescent panel to which such an organic electroluminescent device is applied can also maximize its performance.
- the compound may be represented by any one of the following formulas (2) to (4)
- L 1 to L 3 Z 1 to Z 3, R 1, R 2 , Ar 1 and Ar 2 each are as defined in formula (I).
- n, L 1 to L 3, R 1, R 2 , Ar 1 and Ar 2 each are as defined in formula (I).
- each of R 1 to R 3 is independently selected from the group consisting of a C 1 to C 40 alkyl group, a C 6 to C 60 aryl group, and a heteroaryl group having 5 to 60 nuclear atoms Selected,
- the alkyl, aryl and heteroaryl groups of R 1 to R 3 are each independently selected from the group consisting of a C 1 to C 40 alkyl group, a C 6 to C 60 aryl group, and a heteroaryl group having 5 to 60 nuclear atoms. And when they are substituted with a plurality of substituents, they are the same as or different from each other.
- R 1 to R 3 each independently represents a hydrogen atom, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthalenyl group, , A group selected from the group consisting of triphenylenyl, pyridinyl, pyrimidinyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, fluorenyl, spirofluorenyl and dibenzodioxinyl groups Selected,
- the R 1 to R 3 may have a substituent such as a methyl group, ethyl group, propyl group, butyl group, pentyl group, phenyl group, biphenyl group, terphenyl group, naphthalenyl group, phenanthrenyl group, triphenylenyl group, pyridinyl group,
- a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, a fluorenyl group, a spirofluorenyl group and a dibenzodioxinyl group are each independently a C 1 to C 40 alkyl group, a C 6 to C 60 aryl substituted with an amine group, C 6 ⁇ C 60 aryl group and a nuclear atoms least one member selected from 5 to 60 heteroaryl group the group consisting of substituted or is unsubstituted, in the case where the substitution of a plurality of substituents
- R 1 to R 3 each independently represents a hydrogen atom, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthalenyl group, , A group selected from the group consisting of triphenylenyl, pyridinyl, pyrimidinyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, fluorenyl, spirofluorenyl and dibenzodioxinyl groups Selected,
- the R 1 to R 3 may have a substituent such as a methyl group, ethyl group, propyl group, butyl group, pentyl group, phenyl group, biphenyl group, terphenyl group, naphthalenyl group, phenanthrenyl group, triphenylenyl group, pyridinyl group,
- a dibenzothiophenyl group, a carbazolyl group, a fluorenyl group, a spirofluorenyl group and a dibenzodioxinyl group are each independently a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a phenyl group,
- the aryl group include a biphenyl group, a terphenyl group, a naphthalenyl group, a phenanthrenyl group, a triphenylenyl group
- L 1 and L 3 each independently represent a single bond, a phenylene group, a biphenylene group, a pyridinyl group, a pyrimidinyl group, a naphthalenyl group, a fluorenyl group, A dibenzofuranyl group, and a dibenzothiophenylene group;
- L 2 is selected from the group consisting of phenylene, biphenylene, pyridinyl, pyrimidinyl, naphthalenyl, fluorenyl, carbazolyl, dibenzofuranyl and dibenzothiophenylene;
- the phenylene group, biphenylene group, pyridinyl group, pyrimidinyl group, naphthalenyl group, fluorenyl group, carbazolyl group, dibenzofuranyl group and dibenzothiophenylene group of L 1 to L 3 are each independently C 1 ⁇ C 40 alkyl group, substituted with one substituent at least one selected from the group consisting of C 6 ⁇ C 60 aryl group and the number of nuclear atoms of 5 to 60 heteroaryl group, or is unsubstituted, in the case where the substitution of a plurality of substituents, these are together The same or different.
- L 1 and L 3 are each independently a single bond or a linker selected from the group consisting of the following formulas A-1 to A-4, preferably a single bond, May be a linker represented by the following formula (A-1) or (A-2):
- the linker represented by A-1 may be a linker represented by the following formula (B-1) or (B-2)
- L < 2 > may be a linker represented by the following formula A-3 or A-4:
- L 2 may be a linker selected from the group consisting of the following formulas C-1 to C-4:
- Ar 1 and Ar 2 are each independently selected from the group consisting of a C 1 to C 40 alkyl group, a C 6 to C 60 aryl group and a heteroaryl group having 5 to 60 nuclear atoms
- the alkyl, aryl and heteroaryl groups of Ar 1 and Ar 2 are each independently selected from the group consisting of a C 1 to C 40 alkyl group, a C 6 to C 60 aryl group, and a heteroaryl group having 5 to 60 nuclear atoms , And when they are substituted with a plurality of substituents, they are the same as or different from each other.
- Ar 1 and Ar 2 each independently represent a hydrogen atom, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthalenyl group, , A group selected from the group consisting of triphenylenyl, pyridinyl, pyrimidinyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, fluorenyl, spirofluorenyl and dibenzodioxinyl groups Selected,
- Examples of the groups represented by Ar 1 and Ar 2 include methyl, ethyl, propyl, butyl, pentyl, phenyl, biphenyl, terphenyl, naphthalenyl, phenanthrenyl,
- a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, a fluorenyl group, a spirofluorenyl group and a dibenzodioxinyl group are each independently a C 1 to C 40 alkyl group, a C 6 to C 60 aryl substituted with an amine group, C 6 ⁇ C 60 aryl group and a nuclear atoms least one member selected from 5 to 60 heteroaryl group the group consisting of substituted or is unsubstituted, in the case where the substitution of a plurality of substituents, they are same or different, Do.
- Ar 1 and Ar 2 each independently represent a hydrogen atom, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthalenyl group, , A group selected from the group consisting of triphenylenyl, pyridinyl, pyrimidinyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, fluorenyl, spirofluorenyl and dibenzodioxinyl groups Selected,
- Examples of the groups represented by Ar 1 and Ar 2 include methyl, ethyl, propyl, butyl, pentyl, phenyl, biphenyl, terphenyl, naphthalenyl, phenanthrenyl,
- a dibenzothiophenyl group, a carbazolyl group, a fluorenyl group, a spirofluorenyl group and a dibenzodioxinyl group are each independently a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a phenyl group
- Examples of the aryl group include a biphenyl group, a terphenyl group, a naphthalenyl group, a phenanthrenyl group, a triphenylenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group,
- Ar 1 and Ar 2 each independently may be a substituent represented by any one of the following formulas D-1 to D-7:
- p is an integer from 0 to 5;
- q is an integer from 0 to 4.
- R 4 is hydrogen, deuterium, a halogen, a cyano group, a nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 60 of the aryl group, nuclear atoms of 5 to 60 heteroaryl group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 alkyloxy group of, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group , C 6 to C 60 arylamine groups, C 1 to C 40 alkylsilyl groups, C 1 to C 40 alkylboron groups, C 6 to C 60 arylboron groups, C 6 to C 60 arylphospha group, C 6 ⁇ C 60 mono or diaryl the Phosphinicosuccinic selected from the group the group consisting of C 6 ⁇ with an aryl silyl group of C
- R 4 is C 1 ⁇ alkyl group of C 40, C 6 ⁇ C 60 aryl group and a nuclear atoms selected from 5 to 60 heteroaryl group the group consisting of, wherein R 4 Each of the alkyl group, aryl group and heteroaryl group is independently substituted with at least one substituent selected from the group consisting of a C 1 to C 40 alkyl group, a C 6 to C 60 aryl group, and a heteroaryl group having 5 to 60 ring atoms And when they are unsubstituted and substituted with a plurality of substituents, they are the same as or different from each other.
- R 4 represents a hydrogen atom, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthalenyl group, a phenanthrenyl group, Is selected from the group consisting of pyridinyl, pyrimidinyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, fluorenyl, spirofluorenyl and dibenzodioxinyl groups,
- R 4 may be substituted with a substituent such as a methyl group, ethyl group, propyl group, butyl group, pentyl group, phenyl group, biphenyl group, terphenyl group, naphthalenyl group, phenanthrenyl group, triphenylenyl group, pyridinyl group,
- a dibenzothiophenyl group, a carbazolyl group, a fluorenyl group, a spirofluorenyl group and a dibenzodioxinyl group are each independently a C 1 to C 40 alkyl group, a C 6 to C 60 arylamine group, substituted from the group C 6 ⁇ C 60 aryl group and the number of nuclear atoms of 5 to 60 heteroaryl group comprising one or more substituents selected or is unsubstituted, in the case where the substitution of a plurality of substituents, they are same as or different from
- the compounds represented by formula (1) of the present invention can be represented by the following compounds, but are not limited thereto:
- the compounds of formula 1 of the present invention can be synthesized according to the general synthetic methods ( Chem. Rev. , 60 : 313 (1960); J. Chem. SOC . 4482 (1955); Chem. Rev. 95: 2457 (1995 ). Detailed synthesis of the compound of the present invention will be described in detail in Synthesis Examples to be described later.
- organic electroluminescent device comprising the compound represented by the general formula (1) according to the present invention described above.
- the present invention is an organic electroluminescent device comprising an anode, a cathode, and one or more organic layers sandwiched between the anode and the cathode, wherein at least one of the one or more organic layers includes Include compounds represented by the above formula (1).
- the compounds may be used singly or in combination of two or more.
- the at least one organic material layer may be at least one of a hole injecting layer, a hole transporting layer, a light emitting layer, a light emitting auxiliary layer, an electron transporting layer, an electron transporting auxiliary layer and an electron injecting layer. ≪ / RTI > compounds.
- the structure of the organic electroluminescent device according to the present invention is not particularly limited.
- the organic layer 30 may include a hole transport layer 31, a light emitting layer 32, and an electron transport layer 34.
- a hole transporting auxiliary layer 33 may be interposed between the hole transporting layer 31 and the light emitting layer 32.
- An electron transporting auxiliary layer 35 may be interposed between the electron transporting layer 34 and the light emitting layer 32 can do.
- the organic layer 30 may further include a hole injection layer 37 between the hole transport layer 31 and the anode 10, and the electron transport layer 34 and the cathode And an electron injection layer (36) may be further included between the first electrode (20) and the second electrode (20).
- the hole injection layer 37 deposited between the hole transport layer 31 and the anode 10 improves the interfacial properties between the ITO used as the anode and the organic material used as the hole transport layer 31 But the surface of the ITO layer is applied to the upper surface of the ITO which is not planarized to soften the surface of the ITO.
- the layer can be used without any particular limitation as long as it is commonly used in the art. For example, an amine compound can be used But is not limited thereto.
- the electron injecting layer 36 is a layer which is stacked on the electron transporting layer to facilitate injection of electrons from the cathode to ultimately improve the power efficiency.
- LiF, Liq, NaCl, CsF, Li 2 O, BaO, or the like can be used.
- the light emitting layer 32 may further include a light emitting auxiliary layer between the hole transporting auxiliary layer 33 and the light emitting layer 32.
- the light-emission-assisting layer may serve to adjust the thickness of the organic layer 30 while serving to transport holes to the light-emitting layer 32.
- the light-emission-assisting layer may include a hole-transporting material and may be made of the same material as the hole-transporting layer 31.
- an electron transporting auxiliary layer may be further included between the electron auxiliary layer 35 and the light emitting layer 32. Holes migrating to the ionization potential level in the organic light emitting element by the light emitting layer 32 are blocked by the high energy barrier of the electron transporting layer and can not diffuse or move to the electron transporting layer and consequently have the function of limiting the holes to the light emitting layer do.
- the function of restricting the holes to the light emitting layer prevents diffusion of holes to the electron transporting layer that transports electrons by reduction, thereby suppressing the lifetime degradation due to the irreversible decomposition reaction by oxidation and contributing to improvement in the lifetime of the organic light emitting device .
- the compound represented by formula (1) of the present invention has a basic skeleton by linking an indene derivative containing at least one nitrogen (N) and a phenylene group substituted by one or more cyano groups through a linker.
- Compounds represented by formula (1) having such a structure are electrochemically stable, electron mobility is superior as well as high glass transition temperature and thermal stability as compared with conventionally known six-membered heterocyclic structures. Further, by introducing a cyano group, which is a functional group having a strong electron-attracting ability, two or more electron-withdrawing groups (EWG) can be provided to improve the electron transfer rate, so that it can have physicochemical properties more suitable for electron injection and electron transport layer .
- EWG electron-withdrawing groups
- the compound of the formula (1) of the present invention when used for an organic electroluminescent device, excellent thermal stability and carrier transport ability (in particular, electron transporting ability and light emitting ability) can be expected as well as driving voltage, Can be improved, and high triple-energetic energy can represent an excellent efficiency increase due to the triplet-triplet fusion (TTF) effect as the latest ETL material.
- TTF triplet-triplet fusion
- the compound represented by the formula (1) of the present invention can be used as any one of a hole injection layer, a hole transporting layer, a light emitting layer, an electron transporting layer and an electron injecting layer which are organic compound layers of an organic electroluminescent device.
- Transporting layer and an electron transporting layer and more preferably an electron transporting layer, or an electron transporting layer.
- the compound represented by the above formula (1) can be used as a phosphorescent host, a fluorescent host or a dopant material of a light emitting layer, Preferably a blue phosphorescent host material.
- the organic electroluminescent device according to the present invention may further include an insulating layer or an adhesive layer at the interface between the electrode and the organic layer as well as the anode, one or more organic layers and the cathode sequentially laminated as described above.
- the organic electroluminescent device of the present invention includes materials and methods known in the art, except that at least one or more of the organic material layers (for example, the electron transporting auxiliary layer) is formed to include the compound represented by Formula 1 To form another organic material layer and an electrode.
- the organic material layers for example, the electron transporting auxiliary layer
- the organic material layer may be formed by a vacuum deposition method or a solution coating method.
- the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.
- the substrate usable in the present invention is not particularly limited, and a silicon wafer, quartz, a glass plate, a metal plate, a plastic film and a sheet can be used.
- the anode material may be made of a conductor having a high work function to facilitate injection of holes, for example, metals such as vanadium, chromium, copper, zinc, and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO 2: a combination of a metal and an oxide such as Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole or polyaniline; And carbon black, but are not limited thereto.
- metals such as vanadium, chromium, copper, zinc, and gold or alloys thereof
- Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO)
- ZnO Al or SnO 2: a combination of a metal and an oxide
- the negative electrode material may be made of a conductor having a low work function so as to facilitate electron injection and may be made of a material having a low work function such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, The same metal or an alloy thereof; And multi-layer structure materials such as LiF / Al or LiO 2 / Al, but are not limited thereto.
- Step 1 of [Preparation Example 1] was repeated except for using 2-amino-3-bromopyridine as a reactant to obtain 32 g (yield: 88%) of the desired compound.
- Step 2 of Preparation Example 1 The procedure of Step 2 of Preparation Example 1 was repeated except for using N - [[(3-bromo-2-pyridinyl) amino] thioxomethyl] - ethyl ester as a reactant, 20.2 g (yield 90%) was obtained.
- Step 3 of [Preparation Example 1] was repeated except for using 2-bromo- [1,2,4] triazolo [1,5-a] pyridine as a reactant to obtain the title compound (14.2 g, 65%).
- Step 1 of [Preparation Example 1] was repeated except for using 2-amino-3,5-dichloropyridine as a reactant to obtain 48 g of the title compound (yield 92%).
- Step 3 of [Preparation Example 2] was repeated except for using (4- (4-chloronaphthalen-1-yl) phenyl) boronic acid as a reactant to obtain the desired compound (15.8 g, yield 63%).
- Step 3 of [Preparation Example 2] was repeated except for using (3- (4-chloronaphthalen-1-yl) phenyl) boronic acid as a reactant to obtain 19.5 g of the title compound 58%).
- Step 3 of [Preparation Example 2] was repeated except for using (4- (5-chloronaphthalen-1-yl) phenyl) boronic acid as a reactant to obtain 19.5 g of the desired compound 58%).
- Step 3 of [Preparation Example 2] was repeated except that Preparation Example 1 and (3- (5-chloronaphthalen-1-yl) phenyl) boronic acid were used as a reaction product to obtain 25.5 g 49%).
- Step 3 of [Preparation Example 2] was repeated except that Preparation Example 1 was used and (4- (6-chloronaphthalen-2-yl) phenyl) boronic acid was used as a reactant to obtain the title compound (14.2 g, 70%).
- Step 3 of [Preparation Example 2] was repeated except that Preparation Example 1 was used and (4- (7-chloronaphthalen-2-yl) phenyl) boronic acid was used as a reaction product to obtain 17.5 g 62%).
- Step 3 of [Preparation Example 2] was repeated except that Preparation Example 1 was used and (3- (7-chloronaphthalen-2-yl) phenyl) boronic acid was used as a reaction product to obtain 17.5 g 62%).
- Step 3 of [Preparation Example 2] was repeated except for using Preparation Example 2 and (4- (4-chloronaphthalen-1-yl) phenyl) boronic acid as a reactant to obtain 21.0 g 55%).
- Step 3 of [Preparation Example 2] was repeated except that in Preparation Example 2 and (3- (5-chloronaphthalen-1-yl) phenyl) boronic acid was used, 18.2 g of the title compound 50%).
- Step 3 of [Preparation Example 2] was repeated except that Preparation Example 2 and (3- (7-chloronaphthalen-2-yl) phenyl) boronic acid were used as reaction materials to obtain 13.5 g of the title compound 49%).
- Step 3 of [Preparation Example 2] was repeated except that in Preparation Example 3 and (4- (6-chloronaphthalen-2-yl) phenyl) boronic acid was used, 16.5 g 58%).
- Step 3 of [Preparation Example 2] was repeated except that in Preparation Example 3 and (3- (7-chloronaphthalen-2-yl) phenyl) boronic acid was used, 11.8 g 49%).
- Step 3 of [Preparation Example 2] was repeated except that in Preparation Example 4 and (4- (4-chloronaphthalen-1-yl) phenyl) boronic acid was used, 20.4 g 65%).
- Step 3 of [Preparation Example 2] was repeated except that in Preparation Example 4 and (3- (5-chloronaphthalen-1-yl) phenyl) boronic acid was used, 18.4 g 70%).
- Step 3 of [Preparation Example 2] was repeated except that Preparation Example 4 was used and (4- (6-chloronaphthalen-2-yl) phenyl) boronic acid was used as a reaction product to obtain 15.5 g 59%).
- Step 3 of [Preparation Example 2] was repeated except that Preparation Example 4 was used and (4- (6-chloronaphthalen-2-yl) phenyl) boronic acid was used as a reaction product to obtain 21.2 g 70%).
- Step 3 of [Preparation Example 2] was repeated except that in Preparation Example 4 and (4- (5-chloronaphthalen-1-yl) phenyl) boronic acid was used, 13.4 g 51%).
- Example 6 Preparation of a reaction product of 2- (3- (4-chloro-1-yl) phenyl) - [l, 2,4] triazolo [1,5-a] pyridine and (4'-cyano- [ The procedure of Step 3 of [Preparation Example 4] was repeated except for using 1,1'-biphenyl] -3-yl) boronic acid to obtain 6.0 g (yield 47%) of the target compound.
- Example 19 by reaction of 2- (4- (4-chloro-1-yl) phenyl) - 6, 8-diphenyl- [1,2,4] triazolo [1,5-a] pyridine and ( The procedure of Step 3 of [Preparation Example 4] was repeated except for using 4'-cyano- [1,1'-biphenyl] -4-yl) boronic acid to obtain 5.3 g of the desired compound %).
- Example 19 by reaction of 2- (4- (4-chloro-1-yl) phenyl) - 6, 8-diphenyl- [1,2,4] triazolo [1,5-a] pyridine and ( The procedure of Step 3 of [Preparation Example 4] was repeated except for using 3 ', 5'-dicyano- [1,1'-biphenyl] -4-yl) boronic acid to obtain 5.0 g (Yield: 45%).
- Example 20 by reaction of 2- (3- (5-chloro-1-yl) phenyl) - 6, 8-diphenyl- [1,2,4] triazolo [1,5-a] pyridine and ( The procedure of Step 3 of [Preparation Example 4] was repeated except for using 4-cyanophenyl) boronic acid to obtain the desired compound (6.6 g, yield 52%).
- NPB, ADN and Alq 3 used in this case are as follows.
- a blue organic electroluminescent device was fabricated in the same manner as in Example 1 except that the compound shown in Table 1 was used as the electron transport layer material instead of the compound 2 used in Example 1.
- a blue organic electroluminescent device was fabricated in the same manner as in Example 1, except that Alq 3 , which is an electron transporting layer material, was deposited at a thickness of 30 nm.
- the driving voltage, current efficiency, and emission wavelength at the current density of 10 mA / cm 2 were measured for the organic electroluminescent devices manufactured in Examples 1 to 13 and Comparative Example 1, respectively, and the results are shown in Table 1 below.
- Example 1 Compound 2 3.8 452 8.8 Example 2 Compound 7 3.9 453 8.5 Example 3 Compound 12 4.1 450 9.0 Example 4 Compound 22 4.2 452 8.5 Example 5 Compound 32 3.5 452 8.1 Example 6 Compound 42 3.4 453 8.9 Example 7 Compound 70 3.6 450 8.2 Example 8 Compound 75 4.0 450 8.2 Example 9 Compound 102 3.8 451 8.9 Example 10 Compound 119 3.3 452 9.1 Example 11 Compound 127 3.4 451 8.8 Example 12 Compound 142 3.8 452 8.9 Example 13 Compound 167 3.5 450 8.5 Comparative Example 1 Alq 3 4.8 457 5.8
- NPB, ADN and Alq 3 used in this case are as follows.
- a blue organic electroluminescent device was fabricated in the same manner as in Example 14, except that the compound shown in Table 2 was used instead of the compound 5 used in Example 14 as an electron transporting auxiliary layer material.
- Example 14 The procedure of Example 14 was repeated except that the compound 5 used as the electron transporting auxiliary layer material in Example 14 was not used and the electron transporting layer material Alq 3 was deposited at 30 nm instead of 25 nm, A light emitting device was fabricated.
- the driving voltage, the emission wavelength, the current efficiency and the emission wavelength at the current density of 10 mA / cm 2 were measured for the organic electroluminescent devices manufactured in Examples 14 to 24 and Comparative Example 2, Respectively.
- Example 14 Compound 5 3.5 450 8.5
- Example 15 Compound 18 3.6 450 8.8
- Example 16 Compound 40 3.3 452 8.6
- Example 17 Compound 53 3.8 451 9.0
- Example 18 Compound 65 3.6 450 9.2
- Example 19 Compound 84 4.0 450 8.5
- Example 20 Compound 90 3.8 452 8.4
- Example 21 Compound 113 3.4 452 8.9
- Example 22 Compound 122 3.3 451 8.6
- Example 23 Compound 133 3.7 452 8.2
- Example 24 Compound 165 3.9 450 8.8 Comparative Example 2 - 4.8 457 5.8
- the blue organic electroluminescent devices of Examples 14 to 24 including the electron transporting auxiliary layer formed of the compound according to the present invention had the electron transporting layer of Alq 3 without the electron transporting auxiliary layer,
- the organic EL device of the present invention exhibits excellent current efficiency and excellent driving voltage.
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Abstract
The present invention relates to a novel compound and an organic electroluminescent device comprising the same. As the compound according to the present invention is used for an organic compound layer of an organic electroluminescent device, preferably for a light emitting layer, it is possible to improve the luminous efficiency, driving voltage, and lifetime of the organic electroluminescent device.
Description
본 발명은 유기 전계 발광 소자용 재료로서 사용될 수 있는 신규 유기 화합물 및 이를 포함하는 유기 전계 발광 소자에 관한 것이다.The present invention relates to a novel organic compound that can be used as a material for an organic electroluminescence device and an organic electroluminescence device including the same.
1950년대 베르나노스(Bernanose)의 유기 박막 발광 관측을 시점으로 하여, 1965년 안트라센 단결정을 이용한 청색 전기발광으로 이어진 유기 전계 발광(electroluminescent, EL) 소자에 대한 연구가 이어져 오다가, 1987년 탕(Tang)에 의하여 정공층과 발광층의 기능층으로 나눈 적층 구조의 유기 전계 발광 소자가 제시되었다. 이후, 고효율, 고수명의 유기 전계 발광 소자를 만들기 위하여, 소자 내 각각의 특징적인 유기물층을 도입하는 형태로 발전하여 왔으며, 이에 사용되는 특화된 물질의 개발로 이어졌다.The electroluminescent (EL) devices that led to blue electroluminescence using anthracene single crystals in 1965 were followed up with the observation of organic thin film emission from Bernanose in the 1950s. In 1987, And a functional layer of a light-emitting layer. Thereafter, in order to form a high efficiency and high number of organic electroluminescent devices, each organic material layer has been developed into a form in which each organic material layer has been introduced into the device, leading to the development of specialized materials used therefor.
유기 전계 발광 소자는 두 전극 사이에 전압을 걸어주면 양극에서는 정공이 유기물층으로 주입되고, 음극에서는 전자가 유기물층으로 주입된다. 주입된 정공과 전자가 만났을 때 엑시톤(exciton)이 형성되며, 이 엑시톤이 바닥상태로 떨어질 때 빛이 나게 된다. 이때, 유기물층으로 사용되는 물질은 그 기능에 따라, 발광 물질, 정공 주입 물질, 정공 수송 물질, 전자 수송 물질, 전자 주입 물질 등으로 분류될 수 있다.In the organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected into the organic layer in the anode, and electrons are injected into the organic layer in the cathode. When the injected holes and electrons meet, an exciton is formed. When the exciton falls to the ground state, light is emitted. At this time, the material used as the organic material layer can be classified into a light emitting material, a hole injecting material, a hole transporting material, an electron transporting material, an electron injecting material and the like depending on its function.
발광 물질은 발광색에 따라 청색, 녹색, 적색 발광 물질과, 보다 나은 천연색을 구현하기 위한 노란색 및 주황색 발광 물질로 구분될 수 있다. 또한, 색순도의 증가와 에너지 전이를 통한 발광 효율을 증가시키기 위하여, 발광 물질로서 호스트/도펀트 계를 사용할 수 있다.The luminescent material can be classified into blue, green and red luminescent materials according to luminescent colors and yellow and orange luminescent materials to realize better natural colors. Further, in order to increase the color purity and increase the luminous efficiency through energy transfer, a host / dopant system can be used as a light emitting material.
도펀트 물질은 유기 물질을 사용하는 형광 도펀트와 Ir, Pt 등의 중원자(heavy atoms)가 포함된 금속 착체 화합물을 사용하는 인광 도펀트로 나눌 수 있다. 이때, 인광 재료의 개발은 이론적으로 형광에 비해 4배까지 발광 효율을 향상시킬 수 있기 때문에, 인광 도펀트 뿐만 아니라 인광 호스트 재료들에 대한 연구도 많이 진행되고 있다.The dopant material can be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. At this time, since the development of the phosphorescent material can theoretically improve the luminous efficiency up to 4 times as compared with the fluorescence, the phosphorescent dopant as well as phosphorescent host materials are being studied extensively.
현재까지 정공 주입층, 정공 수송층, 정공 차단층, 전자 수송층 재료로는 NPB, BCP, Alq3 등이 널리 알려져 있으며, 발광층 재료로는 안트라센 유도체들이 보고되고 있다. 특히, 발광층 재료 중 효율 향상 측면에서 장점을 가지고 있는 Firpic, Ir(ppy)3, (acac)Ir(btp)2 등과 같은 Ir을 포함하는 금속 착체 화합물이 청색(blue), 녹색(green), 적색(red)의 인광 도판트 재료로 사용되고 있으며, 4,4-디카바졸리비페닐(4,4-dicarbazolybiphenyl, CBP)은 인광 호스트 재료로 사용되고 있다.To date, NPB, BCP and Alq 3 have been widely known as the hole injecting layer, the hole transporting layer, the hole blocking layer and the electron transporting layer material, and anthracene derivatives have been reported as the light emitting layer material. Particularly, metal complex compounds containing Ir such as Firpic, Ir (ppy) 3 , (acac) Ir (btp) 2 and the like having advantages in terms of efficiency improvement of the light emitting layer material are blue, green, 4,4-dicarbazolybiphenyl (CBP) is used as a phosphorescent dopant material for red phosphorescent dopants.
그러나 종래의 유기물층 재료들은 발광 특성 측면에서는 유리한 면이 있으나, 유리전이온도가 낮아 열적 안정성이 매우 좋지 않기 때문에, 유기 전계 발광 소자의 수명 측면에서 만족할 만한 수준이 되지 못하고 있다. 따라서, 성능이 뛰어난 유기물층 재료의 개발이 요구되고 있다.However, conventional organic material layers are advantageous from the viewpoint of light emitting properties, but their thermal stability is not very good due to their low glass transition temperature, and thus they are not satisfactory in terms of lifetime of the organic electroluminescent device. Therefore, development of an organic layer material having excellent performance is required.
본 발명은 유기 전계 발광 소자에 적용할 수 있으며, 정공, 전자 주입 및 수송능, 발광능 등이 모두 우수한 신규 유기 화합물을 제공하는 것을 목적으로 한다. It is an object of the present invention to provide a novel organic compound which can be applied to an organic electroluminescent device and which is excellent in hole, electron injection, transporting ability, and light emitting ability.
또한, 본 발명은 상기 신규 유기 화합물을 포함하여 낮은 구동 전압과 높은 발광 효율을 나타내며 수명이 향상되는 유기 전계 발광 소자를 제공하는 것을 또 다른 목적으로 한다.It is another object of the present invention to provide an organic electroluminescent device including the novel organic compound and exhibiting a low driving voltage and a high luminous efficiency and having an improved lifetime.
상기한 목적을 달성하기 위해, 본 발명은 하기 화학식 1로 표시되는 화합물을 제공한다:In order to achieve the above object, the present invention provides a compound represented by the following formula (1): < EMI ID =
[화학식 1][Chemical Formula 1]
상기 화학식 1에서,In Formula 1,
n은 1 내지 3의 정수이고;n is an integer from 1 to 3;
Z1 내지 Z3은 각각 독립적으로 N 또는 C(R3)이고, 반드시 하나는 N이며;Z 1 to Z 3 are each independently N or C (R 3 ), and one is necessarily N;
L1 및 L3는 각각 독립적으로 단일결합, C6~C18의 아릴렌기 및 핵원자수 5 내지 18개의 헤테로아릴렌기로 이루어진 군에서 선택되고; L 1 and L 3 are each independently selected from the group consisting of a single bond, a C 6 to C 18 arylene group and a heteroarylene group having 5 to 18 nucleus atoms;
L2는 C6~C18의 아릴렌기 또는 핵원자수 5 내지 18개의 헤테로아릴렌기이며;L 2 is an arylene group having 6 to 18 carbon atoms or a heteroarylene group having 5 to 18 nuclear atoms;
R1 내지 R3은 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되고, 상기 R3이 복수 개인 경우 이들은 서로 동일하거나 상이하며; R 1 to R 3 are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ of C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 6 ~ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C 1 ~ alkyloxy group of C 40, C 6 ~ aryloxy group of C 60, C 3 ~ C 40 alkylsilyl group, C group 6 ~ C 60 aryl silyl, C 1 ~ arylboronic of C 40 group of an alkyl boron, C 6 ~ C 60 group, C 6 ~ C 60 aryl phosphazene group, is selected from the group consisting of an aryl amine of the C 6 ~ C 60 mono or diaryl phosphine blood group and a C 6 ~ C 60 of, in the case where the R 3 a plurality individual which the same or different, and ;
Ar1 및 Ar2는 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되고;Ar 1 and Ar 2 are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ of C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 6 ~ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C 1 ~ alkyloxy group of C 40, C 6 ~ aryloxy group of C 60, C 3 ~ C 40 alkylsilyl group, C group 6 ~ C 60 aryl silyl, C 1 ~ arylboronic of C 40 group of an alkyl boron, C 6 ~ C 60 group, C 6 ~ C 60 aryl phosphazene group, C 6 ~ C 60 mono or diaryl phosphine blood group and a C 6 ~ C 60 is selected from the group consisting of an aryl amine;
상기 L1 내지 L3의 아릴렌기 및 헤테로아릴렌기와, 상기 Ar1, Ar2 및 R1 내지 R3의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이하다.Wherein Ar 1 , Ar 2, and Ar 3, which are the above-mentioned L 1 to L 3 arylene group and heteroarylene group, The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkylboron group, arylboron group of R 1 to R 3 A halogen atom, a cyano group, a nitro group, a C 1 to C 40 alkyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkenyl group, a substituted or unsubstituted aryl group, ~ C 40 of the alkynyl group, C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 6 ~ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C 1 ~ alkyloxy of C 40, C 6 ~ C 60 of the aryloxy group, an alkyl boronic of C 3 ~ C 40 alkylsilyl group, a group C 6 ~ C 60 aryl silyl, C 1 ~ C 40 group, C 6 ~ for C 60 aryl boron group, C 6 ~ C 60 aryl phosphazene group, one member selected from the group consisting of C 6 ~ C 60 mono or diaryl phosphine of blood group and a C 6 ~ C 60 aryl amine of the And when they are substituted with a plurality of substituents, they are the same as or different from each other.
본 발명은 양극, 음극 및 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하며, 상기 1층 이상의 유기물층 중에서 적어도 하나는 상기 화학식 1의 화합물을 포함하는 유기 전계 발광 소자를 제공한다.The present invention provides an organic electroluminescent device including a cathode, a cathode, and at least one organic layer interposed between the anode and the cathode, wherein at least one of the organic layers includes one or more compounds represented by Formula 1 .
본 발명에서의 “알킬”은 탄소수 1 내지 40개의 직쇄 또는 측쇄의 포화 탄화수소에서 유래되는 1가의 치환기이며, 이의 예로는 메틸, 에틸, 프로필, 이소부틸, sec-부틸, 펜틸, iso-아밀, 헥실 등이 있는데, 이에 한정되지 않는다."Alkyl" in the present invention is a monovalent substituent derived from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms, and examples thereof include methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl And the like, but are not limited thereto.
본 발명에서의 “알케닐(alkenyl)”은 탄소-탄소 이중 결합을 1개 이상 가진, 탄소수 2 내지 40개의 직쇄 또는 측쇄의 불포화 탄화수소에서 유래되는 1가의 치환기이며, 이의 예로는 비닐(vinyl), 알릴(allyl), 이소프로펜일(isopropenyl), 2-부텐일(2-butenyl) 등이 있는데, 이에 한정되지 않는다.As used herein, the term " alkenyl " is a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon double bond. Examples thereof include vinyl, But are not limited to, allyl, isopropenyl, 2-butenyl, and the like.
본 발명에서의 “알키닐(alkynyl)”은 탄소-탄소 삼중 결합을 1개 이상 가진, 탄소수 2 내지 40개의 직쇄 또는 측쇄의 불포화 탄화수소에서 유래되는 1가의 치환기이며, 이의 예로는 에티닐(ethynyl), 2-프로파닐(2-propynyl) 등이 있는데, 이에 한정되지 않는다.The term " alkynyl " in the present invention is a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon triple bond. Examples thereof include ethynyl, , 2-propynyl, and the like, but are not limited thereto.
본 발명에서의 “아릴”은 단독 고리 또는 2 이상의 고리가 조합된, 탄소수 6 내지 60개의 방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 또한, 2 이상의 고리가 서로 축합되어 있고, 고리 형성 원자로서 탄소만을 포함(예를 들어, 탄소수는 8 내지 60개일 수 있음)하고, 분자 전체가 비-방향족성(non-aromacity)를 갖는 1가 치환기도 포함될 수 있다. 이러한 아릴의 예로는 페닐, 나프틸, 페난트릴, 안트릴, 플루오레닐 등이 있는데, 이에 한정되지 않는다.&Quot; Aryl " in the present invention means a monovalent substituent derived from a C6-C60 aromatic hydrocarbon having a single ring or a combination of two or more rings. Further, it is preferable that two or more rings are condensed with each other and only carbon atoms are contained as the ring-forming atoms (for example, the number of carbon atoms may be from 8 to 60) and the whole molecule is a non-aromacity monovalent Substituents may also be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, fluorenyl, and the like.
본 발명에서의 “헤테로아릴”은 핵원자수 5 내지 60개의 모노헤테로사이클릭 또는 폴리헤테로사이클릭 방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 이때, 고리 중 하나 이상의 탄소, 바람직하게는 1 내지 3개의 탄소가 N, O, P, S 및 Se 중에서 선택된 헤테로원자로 치환된다. 또한, 2 이상의 고리가 서로 단순 부착(pendant)되거나 축합되어 있고, 고리 형성 원자로서 탄소 외에 N, O, P, S 및 Se 중에서 선택된 헤테로 원자를 포함하고, 분자 전체가 비-방향족성(non-aromacity)를 갖는 1가 그룹도 포함하는 것으로 해석된다. 이러한 헤테로아릴의 예로는 피리딜, 피라지닐, 피리미디닐, 피리다지닐, 트리아지닐과 같은 6-원 모노사이클릭 고리; 페녹사티에닐(phenoxathienyl), 인돌리지닐(indolizinyl), 인돌릴(indolyl), 퓨리닐(purinyl), 퀴놀릴(quinolyl), 벤조티아졸(benzothiazole), 카바졸릴(carbazolyl)과 같은 폴리사이클릭 고리; 2-퓨라닐, N-이미다졸릴, 2-이속사졸릴, 2-피리디닐, 2-피리미디닐 등이 있는데, 이에 한정되지 않는다."Heteroaryl" in the present invention means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. Wherein one or more carbons, preferably one to three carbons, of the ring are substituted with a heteroatom selected from N, O, P, S and Se. In addition, it is preferable that two or more rings are pendant or condensed with each other, and include hetero atoms selected from N, O, P, S and Se besides carbon as a ring-forming atom, < / RTI > aromacity). Examples of such heteroaryls include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; Such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl, and the like. ring; Imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.
본 발명에서의 “아릴옥시”는 RO-로 표시되는 1가의 치환기로, 상기 R은 탄소수 5 내지 60개의 아릴을 의미한다. 이러한 아릴옥시의 예로는 페닐옥시, 나프틸옥시, 디페닐옥시 등이 있는데, 이에 한정되지 않는다.In the present invention, " aryloxy " means a monovalent substituent represented by RO-, and R represents aryl having 5 to 60 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.
본 발명에서의 “알킬옥시”는 R’O-로 표시되는 1가의 치환기로, 상기 R’는 1 내지 40개의 알킬을 의미하며, 직쇄(linear), 측쇄(branched) 또는 사이클릭(cyclic) 구조를 포함하는 것으로 해석한다. 이러한 알킬옥시의 예로는 메톡시, 에톡시, n-프로폭시, 1-프로폭시, t-부톡시, n-부톡시, 펜톡시 등이 있는데, 이에 한정되지 않는다.The term " alkyloxy " in the present invention means a monovalent substituent group represented by R'O-, wherein R 'represents 1 to 40 alkyl, and may be linear, branched or cyclic . ≪ / RTI > Examples of such alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.
본 발명에서의 “아릴아민”은 탄소수 6 내지 60개의 아릴로 치환된 아민을 의미한다.&Quot; Arylamine " in the present invention means an amine substituted with aryl having 6 to 60 carbon atoms.
본 발명에서의 “시클로알킬”은 탄소수 3 내지 40개의 모노사이클릭 또는 폴리사이클릭 비-방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 이러한 사이클로알킬의 예로는 사이클로프로필, 사이클로펜틸, 사이클로헥실, 놀보닐(norbornyl), 아다만틴(adamantine) 등이 있는데, 이에 한정되지 않는다.&Quot; Cycloalkyl " in the present invention means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyls include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.
본 발명에서의 “헤테로시클로알킬”은 핵원자수 3 내지 40개의 비-방향족 탄화수소로부터 유래된 1가의 치환기를 의미하며, 고리 중 하나 이상의 탄소, 바람직하게는 1 내지 3개의 탄소가 N, O, S 또는 Se와 같은 헤테로 원자로 치환된다. 이러한 헤테로시클로알킬의 예로는 모르폴린, 피페라진 등이 있는데, 이에 한정되지 않는다.&Quot; Heterocycloalkyl " in the present invention means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, wherein at least one of the carbons, preferably one to three carbons, S or Se. ≪ / RTI > Examples of such heterocycloalkyls include, but are not limited to, morpholine, piperazine, and the like.
본 발명에서의 “알킬실릴”은 탄소수 1 내지 40개의 알킬로 치환된 실릴이고, “아릴실릴”은 탄소수 5 내지 60개의 아릴로 치환된 실릴을 의미한다.&Quot; Alkylsilyl " in the present invention is silyl substituted with alkyl having 1 to 40 carbon atoms, and " arylsilyl " means silyl substituted with aryl having 5 to 60 carbon atoms.
본 발명에서의 “축합 고리”는 축합 지방족 고리, 축합 방향족 고리, 축합 헤테로지방족 고리, 축합 헤테로방향족 고리 또는 이들의 조합된 형태를 의미한다.In the present invention, the term "condensed rings" means condensed aliphatic rings, condensed aromatic rings, condensed heteroaliphatic rings, condensed heteroaromatic rings, or a combination thereof.
본 발명의 화합물은 열적 안정성, 캐리어 수송능, 발광능 등이 우수하기 때문에 유기 전계 발광 소자의 유기물층 재료로 유용하게 적용될 수 있다.Since the compound of the present invention is excellent in thermal stability, carrier transport ability, light emitting ability, and the like, it can be effectively applied as an organic material layer material of an organic electroluminescent device.
또한, 본 발명의 화합물을 유기물층에 포함하는 유기 전계 발광 소자는 발광성능, 구동전압, 수명, 효율 등의 측면이 크게 향상되어 풀 칼라 디스플레이 패널 등에 효과적으로 적용될 수 있다.In addition, the organic electroluminescent device including the compound of the present invention in the organic material layer can be effectively applied to a full color display panel, etc. in terms of light emitting performance, driving voltage, lifetime and efficiency.
도 1은 본 발명의 일 실시예에 따른 유기 전계 발광 소자의 단면도를 나타낸 것이다.1 is a cross-sectional view of an organic electroluminescent device according to an embodiment of the present invention.
도 2는 본 발명의 일 실시예에 따른 유기 전계 발광 소자의 단면도를 나타낸 것이다.2 is a cross-sectional view of an organic electroluminescent device according to an embodiment of the present invention.
[부호의 설명][Description of Symbols]
10: 양극 20: 음극10: anode 20: cathode
30: 유기층 31: 정공 수송층30: organic layer 31: hole transport layer
32: 발광층 33: 정공 수송 보조층32: light emitting layer 33: hole transporting auxiliary layer
34: 전자 수송층 35: 전자 수송 보조층34: Electron transport layer 35: Electron transport layer
36: 전자 주입층 37: 정공 주입층36: electron injection layer 37: hole injection layer
이하, 본 발명을 상세히 설명한다.Hereinafter, the present invention will be described in detail.
1.One.
신규 유기 화합물New organic compounds
본 발명의 신규 화합물은 하기 화학식 1로 표시될 수 있다:The novel compounds of the present invention can be represented by the following formula
[화학식 1][Chemical Formula 1]
상기 화학식 1에서,In Formula 1,
n은 1 내지 3의 정수이고;n is an integer from 1 to 3;
Z1 내지 Z3은 각각 독립적으로 N 또는 C(R3)이고, 반드시 하나는 N이며;Z 1 to Z 3 are each independently N or C (R 3 ), and one is necessarily N;
L1 및 L3는 각각 독립적으로 단일결합, C6~C18의 아릴렌기 및 핵원자수 5 내지 18개의 헤테로아릴렌기로 이루어진 군에서 선택되고; L 1 and L 3 are each independently selected from the group consisting of a single bond, a C 6 to C 18 arylene group and a heteroarylene group having 5 to 18 nucleus atoms;
L2는 C6~C18의 아릴렌기 또는 핵원자수 5 내지 18개의 헤테로아릴렌기이며;L 2 is an arylene group having 6 to 18 carbon atoms or a heteroarylene group having 5 to 18 nuclear atoms;
R1 내지 R3은 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되고, 상기 R3이 복수 개인 경우 이들은 서로 동일하거나 상이하며; R 1 to R 3 are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ of C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 6 ~ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C 1 ~ alkyloxy group of C 40, C 6 ~ aryloxy group of C 60, C 3 ~ C 40 alkylsilyl group, C group 6 ~ C 60 aryl silyl, C 1 ~ arylboronic of C 40 group of an alkyl boron, C 6 ~ C 60 group, C 6 ~ C 60 aryl phosphazene group, is selected from the group consisting of an aryl amine of the C 6 ~ C 60 mono or diaryl phosphine blood group and a C 6 ~ C 60 of, in the case where the R 3 a plurality individual which the same or different, and ;
Ar1 및 Ar2는 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되고;Ar 1 and Ar 2 are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ of C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 6 ~ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C 1 ~ alkyloxy group of C 40, C 6 ~ aryloxy group of C 60, C 3 ~ C 40 alkylsilyl group, C group 6 ~ C 60 aryl silyl, C 1 ~ arylboronic of C 40 group of an alkyl boron, C 6 ~ C 60 group, C 6 ~ C 60 aryl phosphazene group, C 6 ~ C 60 mono or diaryl phosphine blood group and a C 6 ~ C 60 is selected from the group consisting of an aryl amine;
상기 L1 내지 L3의 아릴렌기 및 헤테로아릴렌기와, 상기 Ar1, Ar2 및 R1 내지 R3의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이하다.Wherein Ar 1 , Ar 2, and Ar 3, which are the above-mentioned L 1 to L 3 arylene group and heteroarylene group, The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkylboron group, arylboron group of R 1 to R 3 A halogen atom, a cyano group, a nitro group, a C 1 to C 40 alkyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkenyl group, a substituted or unsubstituted aryl group, ~ C 40 of the alkynyl group, C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 6 ~ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C 1 ~ alkyloxy of C 40, C 6 ~ C 60 of the aryloxy group, an alkyl boronic of C 3 ~ C 40 alkylsilyl group, a group C 6 ~ C 60 aryl silyl, C 1 ~ C 40 group, C 6 ~ for C 60 aryl boron group, C 6 ~ C 60 aryl phosphazene group, one member selected from the group consisting of C 6 ~ C 60 mono or diaryl phosphine of blood group and a C 6 ~ C 60 aryl amine of the And when they are substituted with a plurality of substituents, they are the same as or different from each other.
보다 구체적으로, 본 발명의 화학식 1로 표시되는 화합물은 질소(N)를 1이상 포함하는 인덴 유도체와 시아노기가 1이상 치환된 페닐렌기가 링커를 통해 결합되어 기본 골격을 이룬다.More specifically, the compound represented by the formula (1) of the present invention has a basic skeleton by linking an indene derivative containing at least one nitrogen (N) and a phenylene group substituted by at least one cyano group through a linker.
이러한 구조의 화학식 1로 표시되는 화합물은 기존에 알려진 6원의 헤테로환 구조에 비해 전기화학적으로 안정하고, 전자 이동성이 우수할 뿐만 아니라 높은 유리 전이온도 및 열적 안정이 우수하다. 또한, 전자이동속도를 향상시키기 위하여 강한 전자끌개능력을 가진 작용기인 시아노기를 도입함으로써 전자끌개기(EWG)를 2 이상 포함하여, 전자주입 및 전자수송층에 더욱 적합한 물리화학적 성질을 가질 수 있게 된다.Compounds represented by formula (1) having such a structure are electrochemically stable, electron mobility is superior as well as high glass transition temperature and thermal stability as compared with conventionally known six-membered heterocyclic structures. Further, by introducing a cyano group, which is a functional group having a strong electron-attracting ability, two or more electron-withdrawing groups (EWG) can be provided to improve the electron transfer rate, so that it can have physicochemical properties more suitable for electron injection and electron transport layer .
따라서, 본 발명의 화학식 1 구조의 화합물들은 유기 전계 발광 소자에 사용할 경우, 우수한 열적 안정성 및 캐리어 수송능(특히, 전자 수송능 및 발광능)을 기대할 수 있을 뿐만 아니라 소자의 구동전압, 효율, 수명 등이 향상될 수 있고, 높은 삼중항 에너지에 의해 최신 ETL 재료로서 TTF(triplet-triplet fusion) 효과로 인한 우수한 효율 상승을 나타낼 수 있다.Therefore, when the compound of the formula (1) of the present invention is used for an organic electroluminescent device, excellent thermal stability and carrier transport ability (in particular, electron transporting ability and light emitting ability) can be expected as well as driving voltage, Can be improved, and high triple-energetic energy can represent an excellent efficiency increase due to the triplet-triplet fusion (TTF) effect as the latest ETL material.
또한, 본 발명의 화학식 1로 표시되는 화합물들은 질소(N)를 1이상 포함하는 인덴 유도체에 강한 전자끌개능력을 가진 작용기인 시아노기가 1이상 치환된 페닐렌기가 링커를 통해 결합되어 보다 넓은 밴드갭 값을 보여주며, 치환기의 방향이나 위치에 따라 HOMO 및 LUMO 에너지 레벨을 조절이 용이하다. 이러한 화합물을 사용한 유기 전계 발광 소자에서 높은 전자 수송성을 보일 수 있다.In addition, the compounds represented by formula (1) of the present invention can be produced by coupling a phenylene group substituted with one or more cyano groups, which is a functional group having strong electron-attracting ability, to an indene derivative containing at least one nitrogen (N) It shows the gap value and it is easy to control the HOMO and LUMO energy levels according to the direction or position of the substituent. The organic electroluminescent device using such a compound can exhibit a high electron transporting property.
따라서, 본 발명의 화학식 1로 표시되는 화합물은 유기 전계 발광 소자의 유기물층 재료, 바람직하게는 발광층 재료(청색의 인광 호스트 재료), 전자 수송층/주입층 재료 발광보조층 재료, 전자수송보조층 재료, 더욱 바람직하게는 발광층 재료, 전자 수송층 재료, 전자수송보조층 재료로 사용될 수 있다. 또한, 상기 화학식 1의 화합물을 포함하는 유기 전계 발광 소자는 성능 및 수명 특성이 크게 향상될 수 있고, 이러한 유기 전계 발광 소자가 적용된 풀 칼라 유기 발광 패널도 성능이 극대화될 수 있다.Therefore, the compound represented by the general formula (1) of the present invention can be used as an organic layer material of an organic electroluminescence device, preferably a light emitting layer material (blue phosphorescent host material), an electron transporting layer / injection layer material emitting auxiliary layer material, More preferably, it can be used as a light emitting layer material, an electron transporting layer material, and an electron transporting layer material. In addition, the organic electroluminescent device including the compound of Formula 1 can be greatly improved in performance and lifetime, and the full-color organic luminescent panel to which such an organic electroluminescent device is applied can also maximize its performance.
본 발명의 바람직한 한 구현 예에 따르면, 상기 화합물은 하기 화학식 2 내지 4 중 어느 하나로 표시될 수 있다:According to one preferred embodiment of the present invention, the compound may be represented by any one of the following formulas (2) to (4)
[화학식 2](2)
[화학식 3](3)
[화학식 4][Chemical Formula 4]
상기 화학식 2 내지 4에서,In the above Chemical Formulas 2 to 4,
L1 내지 L3, Z1 내지 Z3, R1, R2, Ar1 및 Ar2 각각은 화학식 1에서 정의된 바와 같다.L 1 to L 3, Z 1 to Z 3, R 1, R 2 , Ar 1 and Ar 2 each are as defined in formula (I).
본 발명의 바람직한 한 구현 예에 따르면, 상기 화합물은 하기 화학식 5로 표시될 수 있다:According to one preferred embodiment of the present invention, the compound may be represented by the following general formula (5): < EMI ID =
[화학식 5][Chemical Formula 5]
상기 화학식 5에서,In Formula 5,
n, L1 내지 L3, R1, R2, Ar1 및 Ar2 각각은 화학식 1에서 정의된 바와 같다.n, L 1 to L 3, R 1, R 2 , Ar 1 and Ar 2 each are as defined in formula (I).
본 발명의 바람직한 한 구현 예에 따르면, 상기 R1 내지 R3은 각각 독립적으로 C1~C40의 알킬기, C6~C60의 아릴기 및 핵원자수 5 내지 60개의 헤테로아릴기로 이루어진 군에서 선택되고, According to a preferred embodiment of the present invention, each of R 1 to R 3 is independently selected from the group consisting of a C 1 to C 40 alkyl group, a C 6 to C 60 aryl group, and a heteroaryl group having 5 to 60 nuclear atoms Selected,
상기 R1 내지 R3의 알킬기, 아릴기 및 헤테로아릴기는 각각 독립적으로 C1~C40의 알킬기, C6~C60의 아릴기 및 핵원자수 5 내지 60개의 헤테로아릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이하다.The alkyl, aryl and heteroaryl groups of R 1 to R 3 are each independently selected from the group consisting of a C 1 to C 40 alkyl group, a C 6 to C 60 aryl group, and a heteroaryl group having 5 to 60 nuclear atoms. And when they are substituted with a plurality of substituents, they are the same as or different from each other.
본 발명의 바람직한 한 구현 예에 따르면, 상기 R1 내지 R3은 각각 독립적으로 수소, 메틸기, 에틸기, 프로필기, 부틸기, 펜틸기, 페닐기, 비페닐기, 터페닐기, 나프탈레닐기, 페난트레닐기, 트리페닐레닐기, 피리디닐기, 피리미디닐기, 트리아지닐기, 디벤조퓨라닐기, 디벤조티오페닐기, 카바졸릴기, 플루오레닐기, 스피로플루오레닐기 및 디벤조디옥시닐기로 이루어진 군에서 선택되며, According to a preferred embodiment of the present invention, R 1 to R 3 each independently represents a hydrogen atom, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthalenyl group, , A group selected from the group consisting of triphenylenyl, pyridinyl, pyrimidinyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, fluorenyl, spirofluorenyl and dibenzodioxinyl groups Selected,
상기 R1 내지 R3의 메틸기, 에틸기, 프로필기, 부틸기, 펜틸기, 페닐기, 비페닐기, 터페닐기, 나프탈레닐기, 페난트레닐기, 트리페닐레닐기, 피리디닐기, 피리미디닐기, 트리아지닐기, 디벤조퓨라닐기, 디벤조티오페닐기, 카바졸릴기, 플루오레닐기, 스피로플루오레닐기 및 디벤조디옥시닐기는 각각 독립적으로 C1~C40의 알킬기, C6~C60의 아릴아민기, C6~C60의 아릴기 및 핵원자수 5 내지 60개의 헤테로아릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이하다.The R 1 to R 3 may have a substituent such as a methyl group, ethyl group, propyl group, butyl group, pentyl group, phenyl group, biphenyl group, terphenyl group, naphthalenyl group, phenanthrenyl group, triphenylenyl group, pyridinyl group, A dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, a fluorenyl group, a spirofluorenyl group and a dibenzodioxinyl group are each independently a C 1 to C 40 alkyl group, a C 6 to C 60 aryl substituted with an amine group, C 6 ~ C 60 aryl group and a nuclear atoms least one member selected from 5 to 60 heteroaryl group the group consisting of substituted or is unsubstituted, in the case where the substitution of a plurality of substituents, they are same or different, Do.
본 발명의 바람직한 한 구현 예에 따르면, 상기 R1 내지 R3은 각각 독립적으로 수소, 메틸기, 에틸기, 프로필기, 부틸기, 펜틸기, 페닐기, 비페닐기, 터페닐기, 나프탈레닐기, 페난트레닐기, 트리페닐레닐기, 피리디닐기, 피리미디닐기, 트리아지닐기, 디벤조퓨라닐기, 디벤조티오페닐기, 카바졸릴기, 플루오레닐기, 스피로플루오레닐기 및 디벤조디옥시닐기로 이루어진 군에서 선택되며, According to a preferred embodiment of the present invention, R 1 to R 3 each independently represents a hydrogen atom, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthalenyl group, , A group selected from the group consisting of triphenylenyl, pyridinyl, pyrimidinyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, fluorenyl, spirofluorenyl and dibenzodioxinyl groups Selected,
상기 R1 내지 R3의 메틸기, 에틸기, 프로필기, 부틸기, 펜틸기, 페닐기, 비페닐기, 터페닐기, 나프탈레닐기, 페난트레닐기, 트리페닐레닐기, 피리디닐기, 피리미디닐기, 트리아지닐기, 디벤조퓨라닐기, 디벤조티오페닐기, 카바졸릴기, 플루오레닐기, 스피로플루오레닐기 및 디벤조디옥시닐기는 각각 독립적으로 메틸기, 에틸기, 프로필기, 부틸기, 펜틸기, 페닐기, 비페닐기, 터페닐기, 나프탈레닐기, 페난트레닐기, 트리페닐레닐기, 피리디닐기, 피리미디닐기, 트리아지닐기, 디벤조퓨라닐기, 디벤조티오페닐기, 카바졸릴기, 플루오레닐기, 스피로플루오레닐기 및 디벤조디옥시닐기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이하다.The R 1 to R 3 may have a substituent such as a methyl group, ethyl group, propyl group, butyl group, pentyl group, phenyl group, biphenyl group, terphenyl group, naphthalenyl group, phenanthrenyl group, triphenylenyl group, pyridinyl group, A dibenzothiophenyl group, a carbazolyl group, a fluorenyl group, a spirofluorenyl group and a dibenzodioxinyl group are each independently a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a phenyl group, Examples of the aryl group include a biphenyl group, a terphenyl group, a naphthalenyl group, a phenanthrenyl group, a triphenylenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, A fluorenyl group and a dibenzodioxynyl group, and when they are substituted with a plurality of substituents, they are the same as or different from each other.
본 발명의 바람직한 한 구현 예에 따르면, 상기 L1 및 L3는 각각 독립적으로 단일결합, 페닐렌기, 비페닐렌기, 피리디닐기, 피리미디닐기, 나프탈레닐기, 플루오레닐기, 카바졸릴기, 디벤조퓨라닐기 및 디벤조티오페닐렌기로 이루어진 군에서 선택되고; According to a preferred embodiment of the present invention, L 1 and L 3 each independently represent a single bond, a phenylene group, a biphenylene group, a pyridinyl group, a pyrimidinyl group, a naphthalenyl group, a fluorenyl group, A dibenzofuranyl group, and a dibenzothiophenylene group;
상기 L2는 페닐렌기, 비페닐렌기, 피리디닐기, 피리미디닐기, 나프탈레닐기, 플루오레닐기, 카바졸릴기, 디벤조퓨라닐기 및 디벤조티오페닐렌기로 이루어진 군에서 선택되며; L 2 is selected from the group consisting of phenylene, biphenylene, pyridinyl, pyrimidinyl, naphthalenyl, fluorenyl, carbazolyl, dibenzofuranyl and dibenzothiophenylene;
상기 L1 내지 L3의 페닐렌기, 비페닐렌기, 피리디닐기, 피리미디닐기, 나프탈레닐기, 플루오레닐기, 카바졸릴기, 디벤조퓨라닐기 및 디벤조티오페닐렌기는 각각 독립적으로 C1~C40의 알킬기, C6~C60의 아릴기 및 핵원자수 5 내지 60개의 헤테로아릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이하다.The phenylene group, biphenylene group, pyridinyl group, pyrimidinyl group, naphthalenyl group, fluorenyl group, carbazolyl group, dibenzofuranyl group and dibenzothiophenylene group of L 1 to L 3 are each independently C 1 ~ C 40 alkyl group, substituted with one substituent at least one selected from the group consisting of C 6 ~ C 60 aryl group and the number of nuclear atoms of 5 to 60 heteroaryl group, or is unsubstituted, in the case where the substitution of a plurality of substituents, these are together The same or different.
본 발명의 바람직한 한 구현 예에 따르면, 상기 L1 및 L3는 각각 독립적으로 단일결합이거나, 하기 화학식 A-1 내지 A-4로 이루어진 군에서 선택된 링커일 수 있고, 바람직하게는 단일결합이거나, 하기 화학식 A-1 또는 A--2로 표시되는 링커일 수 있다:According to a preferred embodiment of the present invention, L 1 and L 3 are each independently a single bond or a linker selected from the group consisting of the following formulas A-1 to A-4, preferably a single bond, May be a linker represented by the following formula (A-1) or (A-2):
상기 화학식 A-1 내지 A-4에서,In the above Formulas A-1 to A-4,
*는 결합이 이루어지는 부분을 의미한다.* Means the part where the combination is made.
본 발명의 바람직한 한 구현 예에 따르면, 상기 A-1로 표시되는 링커는 하기 화학식 B-1 또는 B-2로 표시되는 링커일 수 있다:According to a preferred embodiment of the present invention, the linker represented by A-1 may be a linker represented by the following formula (B-1) or (B-2)
상기 화학식 B-1 또는 B-2에서,In the above formula (B-1) or (B-2)
*는 결합이 이루어지는 부분을 의미한다.* Means the part where the combination is made.
본 발명의 바람직한 한 구현 예에 따르면, 상기 L2는 하기 화학식 A-3 또는 A-4로 표시되는 링커일 수 있다:According to one preferred embodiment of the present invention, L < 2 > may be a linker represented by the following formula A-3 or A-4:
상기 화학식 A-3 및 A-4에서,In the above Formulas A-3 and A-4,
*는 결합이 이루어지는 부분을 의미한다.* Means the part where the combination is made.
본 발명의 보다 바람직한 한 구현 예에 따르면, 상기 L2는 하기 화학식 C-1 내지 C-4로 이루어진 군에서 선택되는 링커일 수 있다:According to one more preferred embodiment of the present invention, L 2 may be a linker selected from the group consisting of the following formulas C-1 to C-4:
상기 화학식 C-1 내지 C-4에서,In the above formulas C-1 to C-4,
*는 결합이 이루어지는 부분을 의미한다.* Means the part where the combination is made.
본 발명의 바람직한 한 구현 예에 따르면, 상기 Ar1 및 Ar2는 각각 독립적으로 C1~C40의 알킬기, C6~C60의 아릴기 및 핵원자수 5 내지 60개의 헤테로아릴기로 이루어진 군에서 선택되고, 상기 Ar1 및 Ar2의 알킬기, 아릴기 및 헤테로아릴기는 각각 독립적으로 C1~C40의 알킬기, C6~C60의 아릴기 및 핵원자수 5 내지 60개의 헤테로아릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이하다.According to a preferred embodiment of the present invention, Ar 1 and Ar 2 are each independently selected from the group consisting of a C 1 to C 40 alkyl group, a C 6 to C 60 aryl group and a heteroaryl group having 5 to 60 nuclear atoms And the alkyl, aryl and heteroaryl groups of Ar 1 and Ar 2 are each independently selected from the group consisting of a C 1 to C 40 alkyl group, a C 6 to C 60 aryl group, and a heteroaryl group having 5 to 60 nuclear atoms , And when they are substituted with a plurality of substituents, they are the same as or different from each other.
본 발명의 바람직한 한 구현 예에 따르면, 상기 Ar1 및 Ar2는 각각 독립적으로 수소, 메틸기, 에틸기, 프로필기, 부틸기, 펜틸기, 페닐기, 비페닐기, 터페닐기, 나프탈레닐기, 페난트레닐기, 트리페닐레닐기, 피리디닐기, 피리미디닐기, 트리아지닐기, 디벤조퓨라닐기, 디벤조티오페닐기, 카바졸릴기, 플루오레닐기, 스피로플루오레닐기 및 디벤조디옥시닐기로 이루어진 군에서 선택되며, According to a preferred embodiment of the present invention, Ar 1 and Ar 2 each independently represent a hydrogen atom, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthalenyl group, , A group selected from the group consisting of triphenylenyl, pyridinyl, pyrimidinyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, fluorenyl, spirofluorenyl and dibenzodioxinyl groups Selected,
상기 Ar1 및 Ar2의 메틸기, 에틸기, 프로필기, 부틸기, 펜틸기, 페닐기, 비페닐기, 터페닐기, 나프탈레닐기, 페난트레닐기, 트리페닐레닐기, 피리디닐기, 피리미디닐기, 트리아지닐기, 디벤조퓨라닐기, 디벤조티오페닐기, 카바졸릴기, 플루오레닐기, 스피로플루오레닐기 및 디벤조디옥시닐기는 각각 독립적으로 C1~C40의 알킬기, C6~C60의 아릴아민기, C6~C60의 아릴기 및 핵원자수 5 내지 60개의 헤테로아릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이하다.Examples of the groups represented by Ar 1 and Ar 2 include methyl, ethyl, propyl, butyl, pentyl, phenyl, biphenyl, terphenyl, naphthalenyl, phenanthrenyl, A dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, a fluorenyl group, a spirofluorenyl group and a dibenzodioxinyl group are each independently a C 1 to C 40 alkyl group, a C 6 to C 60 aryl substituted with an amine group, C 6 ~ C 60 aryl group and a nuclear atoms least one member selected from 5 to 60 heteroaryl group the group consisting of substituted or is unsubstituted, in the case where the substitution of a plurality of substituents, they are same or different, Do.
본 발명의 바람직한 한 구현 예에 따르면, 상기 Ar1 및 Ar2는 각각 독립적으로 수소, 메틸기, 에틸기, 프로필기, 부틸기, 펜틸기, 페닐기, 비페닐기, 터페닐기, 나프탈레닐기, 페난트레닐기, 트리페닐레닐기, 피리디닐기, 피리미디닐기, 트리아지닐기, 디벤조퓨라닐기, 디벤조티오페닐기, 카바졸릴기, 플루오레닐기, 스피로플루오레닐기 및 디벤조디옥시닐기로 이루어진 군에서 선택되며, According to a preferred embodiment of the present invention, Ar 1 and Ar 2 each independently represent a hydrogen atom, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthalenyl group, , A group selected from the group consisting of triphenylenyl, pyridinyl, pyrimidinyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, fluorenyl, spirofluorenyl and dibenzodioxinyl groups Selected,
상기 Ar1 및 Ar2의 메틸기, 에틸기, 프로필기, 부틸기, 펜틸기, 페닐기, 비페닐기, 터페닐기, 나프탈레닐기, 페난트레닐기, 트리페닐레닐기, 피리디닐기, 피리미디닐기, 트리아지닐기, 디벤조퓨라닐기, 디벤조티오페닐기, 카바졸릴기, 플루오레닐기, 스피로플루오레닐기 및 디벤조디옥시닐기는 각각 독립적으로 메틸기, 에틸기, 프로필기, 부틸기, 펜틸기, 페닐기, 비페닐기, 터페닐기, 나프탈레닐기, 페난트레닐기, 트리페닐레닐기, 피리디닐기, 피리미디닐기, 트리아지닐기, 디벤조퓨라닐기, 디벤조티오페닐기, 카바졸릴기, 플루오레닐기, 스피로플루오레닐기 및 디벤조디옥시닐기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이하다.Examples of the groups represented by Ar 1 and Ar 2 include methyl, ethyl, propyl, butyl, pentyl, phenyl, biphenyl, terphenyl, naphthalenyl, phenanthrenyl, A dibenzothiophenyl group, a carbazolyl group, a fluorenyl group, a spirofluorenyl group and a dibenzodioxinyl group are each independently a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a phenyl group, Examples of the aryl group include a biphenyl group, a terphenyl group, a naphthalenyl group, a phenanthrenyl group, a triphenylenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, A fluorenyl group and a dibenzodioxynyl group, and when they are substituted with a plurality of substituents, they are the same as or different from each other.
본 발명의 바람직한 한 구현 예에 따르면, 상기 Ar1 및 Ar2는 각각 독립적으로 하기 화학식 D-1 내지 D-7 중 어느 하나로 표시되는 치환기일 수 있다:According to a preferred embodiment of the present invention, Ar 1 and Ar 2 each independently may be a substituent represented by any one of the following formulas D-1 to D-7:
상기 화학식 D-1 내지 D-7에서,In the above formulas D-1 to D-7,
*은 결합이 이루어지는 부분을 의미하고;* Denotes the part where the bond is made;
p는 0 내지 5의 정수이며;p is an integer from 0 to 5;
q는 0 내지 4의 정수이며;q is an integer from 0 to 4;
R4는 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴아민기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성하고, 상기 R4 가 복수 개인 경우 이들은 서로 동일하거나 상이하며;R 4 is hydrogen, deuterium, a halogen, a cyano group, a nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 6 ~ C 60 of the aryl group, nuclear atoms of 5 to 60 heteroaryl group, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkyloxy group of, C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group , C 6 to C 60 arylamine groups, C 1 to C 40 alkylsilyl groups, C 1 to C 40 alkylboron groups, C 6 to C 60 arylboron groups, C 6 to C 60 arylphospha group, C 6 ~ C 60 mono or diaryl the Phosphinicosuccinic selected from the group the group consisting of C 6 ~ with an aryl silyl group of C 60 or, by combining groups of neighboring case form a condensed ring, and individual said R 4 is a plurality, they Are the same or different from each other;
상기 R4의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이하다.Alkyl groups of the R 4, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group, A halogen atom, a cyano group, a nitro group, a C 1 to C 40 alkyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, A C 6 to C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 6 to C 60 aryloxy group, a C 1 to C 40 alkyloxy group, a C 6 to C 60 C 3 to C 40 cycloalkyl groups, 3 to 40 nucleus atom heterocycloalkyl groups, C 1 to C 40 alkylsilyl groups, C 1 to C 40 alkylboron groups, C 6 to C 60 the arylboronic group, one member selected from the group consisting of C 6 ~ C 60 aryl phosphazene group, C 6 ~ C 60 mono or diaryl phosphine of blood group and a C 6 ~ C 60 aryl group in the silyl Substituted with a substituent being unsubstituted or, if substituted by a plurality of substituents, they are same as or different from each other.
본 발명의 바람직한 한 구현 예에 따르면, 상기 R4 는 C1~C40의 알킬기, C6~C60의 아릴기 및 핵원자수 5 내지 60개의 헤테로아릴기로 이루어진 군에서 선택되고, 상기 R4 의 알킬기, 아릴기 및 헤테로아릴기는 각각 독립적으로 C1~C40의 알킬기, C6~C60의 아릴기 및 핵원자수 5 내지 60개의 헤테로아릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이하다.According to one preferred embodiment of the invention, wherein R 4 is C 1 ~ alkyl group of C 40, C 6 ~ C 60 aryl group and a nuclear atoms selected from 5 to 60 heteroaryl group the group consisting of, wherein R 4 Each of the alkyl group, aryl group and heteroaryl group is independently substituted with at least one substituent selected from the group consisting of a C 1 to C 40 alkyl group, a C 6 to C 60 aryl group, and a heteroaryl group having 5 to 60 ring atoms And when they are unsubstituted and substituted with a plurality of substituents, they are the same as or different from each other.
본 발명의 바람직한 한 구현 예에 따르면, 상기 R4는 수소, 메틸기, 에틸기, 프로필기, 부틸기, 펜틸기, 페닐기, 비페닐기, 터페닐기, 나프탈레닐기, 페난트레닐기, 트리페닐레닐기, 피리디닐기, 피리미디닐기, 트리아지닐기, 디벤조퓨라닐기, 디벤조티오페닐기, 카바졸릴기, 플루오레닐기, 스피로플루오레닐기 및 디벤조디옥시닐기로 이루어진 군에서 선택되며, According to a preferred embodiment of the present invention, R 4 represents a hydrogen atom, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthalenyl group, a phenanthrenyl group, Is selected from the group consisting of pyridinyl, pyrimidinyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, fluorenyl, spirofluorenyl and dibenzodioxinyl groups,
상기 R4 의 메틸기, 에틸기, 프로필기, 부틸기, 펜틸기, 페닐기, 비페닐기, 터페닐기, 나프탈레닐기, 페난트레닐기, 트리페닐레닐기, 피리디닐기, 피리미디닐기, 트리아지닐기, 디벤조퓨라닐기, 디벤조티오페닐기, 카바졸릴기, 플루오레닐기, 스피로플루오레닐기 및 디벤조디옥시닐기는 각각 독립적으로 C1~C40의 알킬기, C6~C60의 아릴아민기, C6~C60의 아릴기 및 핵원자수 5 내지 60개의 헤테로아릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이하다.The above-mentioned R 4 may be substituted with a substituent such as a methyl group, ethyl group, propyl group, butyl group, pentyl group, phenyl group, biphenyl group, terphenyl group, naphthalenyl group, phenanthrenyl group, triphenylenyl group, pyridinyl group, A dibenzothiophenyl group, a carbazolyl group, a fluorenyl group, a spirofluorenyl group and a dibenzodioxinyl group are each independently a C 1 to C 40 alkyl group, a C 6 to C 60 arylamine group, substituted from the group C 6 ~ C 60 aryl group and the number of nuclear atoms of 5 to 60 heteroaryl group comprising one or more substituents selected or is unsubstituted, in the case where the substitution of a plurality of substituents, they are same as or different from each other.
본 발명의 화학식 1로 표시되는 화합물은 하기 화합물로 나타낼 수 있으나 이에 한정되는 것은 아니다: The compounds represented by formula (1) of the present invention can be represented by the following compounds, but are not limited thereto:
본 발명의 화학식 1의 화합물은 일반적인 합성방법에 따라 합성될 수 있다(Chem. Rev., 60:313 (1960); J. Chem. SOC. 4482 (1955); Chem. Rev. 95: 2457 (1995) 등 참조). 본 발명의 화합물에 대한 상세한 합성 과정은 후술하는 합성예에서 구체적으로 기술하도록 한다. The compounds of formula 1 of the present invention can be synthesized according to the general synthetic methods ( Chem. Rev. , 60 : 313 (1960); J. Chem. SOC . 4482 (1955); Chem. Rev. 95: 2457 (1995 ). Detailed synthesis of the compound of the present invention will be described in detail in Synthesis Examples to be described later.
2.2.
유기 전계 발광 소자Organic electroluminescent device
한편, 본 발명의 다른 측면은 상기한 본 발명에 따른 화학식 1로 표시되는 화합물을 포함하는 유기 전계 발광 소자(유기 EL 소자)에 관한 것이다.Another aspect of the present invention relates to an organic electroluminescent device (organic EL device) comprising the compound represented by the general formula (1) according to the present invention described above.
구체적으로, 본 발명은 양극(anode), 음극(cathode), 및 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하는 유기 전계 발광 소자로서, 상기 1층 이상의 유기물층 중 적어도 하나는 상기 화학식 1로 표시되는 화합물을 포함한다. 이때, 상기 화합물은 단독 또는 2 이상 혼합되어 사용될 수 있다.Specifically, the present invention is an organic electroluminescent device comprising an anode, a cathode, and one or more organic layers sandwiched between the anode and the cathode, wherein at least one of the one or more organic layers includes Include compounds represented by the above formula (1). At this time, the compounds may be used singly or in combination of two or more.
상기 1층 이상의 유기물층은 정공 주입층, 정공 수송층, 발광층, 발광 보조층, 전자 수송층, 전자 수송 보조층 및 전자 주입층 중 어느 하나 이상일 수 있고, 이 중에서 적어도 하나의 유기물층이 상기 화학식 1로 표시되는 화합물을 포함할 수 있다. The at least one organic material layer may be at least one of a hole injecting layer, a hole transporting layer, a light emitting layer, a light emitting auxiliary layer, an electron transporting layer, an electron transporting auxiliary layer and an electron injecting layer. ≪ / RTI > compounds.
전술한 본 발명에 따른 유기 전계 발광 소자의 구조는 특별히 한정되지 않으나, 일 예시로 도 1을 참고하면, 예컨대 서로 마주하는 양극(10)과 음극(20), 그리고 상기 양극(10)과 음극(20) 사이에 위치하는 유기층(30)을 포함한다. 여기서, 상기 유기층(30)은 정공 수송층(31), 발광층(32) 및 전자 수송층(34)을 포함할 수 있다. 또한, 상기 정공 수송층(31)과 발광층(32) 사이에는 정공 수송 보조층(33)을 포함할 수 있으며, 상기 전자 수송층(34)과 발광층(32) 사이에는 전자 수송 보조층(35)을 포함할 수 있다. The structure of the organic electroluminescent device according to the present invention is not particularly limited. For example, referring to FIG. 1, an anode 10 and a cathode 20 facing each other, 20). ≪ / RTI > Here, the organic layer 30 may include a hole transport layer 31, a light emitting layer 32, and an electron transport layer 34. A hole transporting auxiliary layer 33 may be interposed between the hole transporting layer 31 and the light emitting layer 32. An electron transporting auxiliary layer 35 may be interposed between the electron transporting layer 34 and the light emitting layer 32 can do.
본 발명의 다른 예시로 도 2를 참고하면, 상기 유기층(30)은 정공 수송층(31)과 양극(10)사이에 정공 주입층(37)을 더 포함할 수 있으며, 전자 수송층(34)과 음극(20)사이에는 전자 주입층(36)을 추가로 더 포함할 수 있다. 2, the organic layer 30 may further include a hole injection layer 37 between the hole transport layer 31 and the anode 10, and the electron transport layer 34 and the cathode And an electron injection layer (36) may be further included between the first electrode (20) and the second electrode (20).
본 발명에서 상기 정공 수송층(31)과 양극(10) 사이에 적층되는 정공 주입층(37)은 양극으로 사용되는 ITO와, 정공 수송층(31)으로 사용되는 유기물질 사이의 계면 특성을 개선할 뿐만 아니라 그 표면이 평탄하지 않은 ITO의 상부에 도포되어 ITO의 표면을 부드럽게 만들어주는 기능을 하는 층으로, 당 기술분야에서 통상적으로 사용되는 것이면 특별한 제한없이 사용할 수 있으며, 예컨대, 아민 화합물을 사용할 수 있으나 이에 한정되는 것은 아니다.In the present invention, the hole injection layer 37 deposited between the hole transport layer 31 and the anode 10 improves the interfacial properties between the ITO used as the anode and the organic material used as the hole transport layer 31 But the surface of the ITO layer is applied to the upper surface of the ITO which is not planarized to soften the surface of the ITO. The layer can be used without any particular limitation as long as it is commonly used in the art. For example, an amine compound can be used But is not limited thereto.
또한, 상기 전자 주입층(36)은 전자 수송층의 상부에 적층되어 음극으로부터의 전자 주입을 용이하게 해주어 궁극적으로 전력효율을 개선시키는 기능을 수행하는 층으로, 당 기술분야에서 통상적으로 사용되는 것이면 특별한 제한없이 사용할 수 있으며, 예컨대, LiF, Liq, NaCl, CsF, Li2O, BaO 등의 물질을 이용할 수 있다. The electron injecting layer 36 is a layer which is stacked on the electron transporting layer to facilitate injection of electrons from the cathode to ultimately improve the power efficiency. For example, LiF, Liq, NaCl, CsF, Li 2 O, BaO, or the like can be used.
또한, 본 발명에서 도면에는 도시하지 않았으나, 상기 정공 수송 보조층(33)과 발광층(32) 사이에 발광 보조층을 더 포함할 수 있다. 상기 발광 보조층은 발광층(32)에 정공을 수송하는 역할을 하면서 유기층(30)의 두께를 조정하는 역할을 할 수 있다. 상기 발광 보조층은 정공 수송 물질을 포함할 수 있고, 정공 수송층(31)과 동일한 물질로 만들어질 수 있다.In addition, although not shown in the drawings, the light emitting layer 32 may further include a light emitting auxiliary layer between the hole transporting auxiliary layer 33 and the light emitting layer 32. The light-emission-assisting layer may serve to adjust the thickness of the organic layer 30 while serving to transport holes to the light-emitting layer 32. The light-emission-assisting layer may include a hole-transporting material and may be made of the same material as the hole-transporting layer 31.
또한, 본 발명에서 도면에는 도시하지 않았으나, 상기 전자 보조층(35)과 발광층(32) 사이에 전자 수송 보조층을 더 포함할 수 있다. 상기 발광층(32)으로 유기 발광 소자 내에서 이온화 포텐셜 레벨을 타고 이동하는 정공이 전자 수송 보조층의 높은 에너지 장벽에 막혀 전자 수송층으로 확산, 또는 이동하지 못해, 결과적으로 정공을 발광층에 제한시키는 기능을 한다. 이렇게 정공을 발광층에 제한시키는 기능은 환원에 의해 전자를 이동시키는 전자 수송층으로 정공이 확산되는 것을 막아, 산화에 의한 비가역적 분해반응을 통한 수명저하 현상을 억제하여, 유기 발광 소자의 수명 개선에 기여할 수 있다.In addition, although not shown in the drawings, an electron transporting auxiliary layer may be further included between the electron auxiliary layer 35 and the light emitting layer 32. Holes migrating to the ionization potential level in the organic light emitting element by the light emitting layer 32 are blocked by the high energy barrier of the electron transporting layer and can not diffuse or move to the electron transporting layer and consequently have the function of limiting the holes to the light emitting layer do. The function of restricting the holes to the light emitting layer prevents diffusion of holes to the electron transporting layer that transports electrons by reduction, thereby suppressing the lifetime degradation due to the irreversible decomposition reaction by oxidation and contributing to improvement in the lifetime of the organic light emitting device .
본 발명의 화학식 1로 표시되는 화합물은 질소(N)를 1이상 포함하는 인덴 유도체와 시아노기가 1이상 치환된 페닐렌기가 링커를 통해 결합되어 기본 골격을 이룬다.The compound represented by formula (1) of the present invention has a basic skeleton by linking an indene derivative containing at least one nitrogen (N) and a phenylene group substituted by one or more cyano groups through a linker.
이러한 구조의 화학식 1로 표시되는 화합물은 기존에 알려진 6원의 헤테로환 구조에 비해 전기화학적으로 안정하고, 전자 이동성이 우수할 뿐만 아니라 높은 유리 전이온도 및 열적 안정이 우수하다. 또한, 전자이동속도를 향상시키기 위하여 강한 전자끌개능력을 가진 작용기인 시아노기를 도입함으로써 전자끌개기(EWG)를 2 이상 포함하여, 전자주입 및 전자수송층에 더욱 적합한 물리화학적 성질을 가질 수 있게 된다.Compounds represented by formula (1) having such a structure are electrochemically stable, electron mobility is superior as well as high glass transition temperature and thermal stability as compared with conventionally known six-membered heterocyclic structures. Further, by introducing a cyano group, which is a functional group having a strong electron-attracting ability, two or more electron-withdrawing groups (EWG) can be provided to improve the electron transfer rate, so that it can have physicochemical properties more suitable for electron injection and electron transport layer .
따라서, 본 발명의 화학식 1 구조의 화합물들은 유기 전계 발광 소자에 사용할 경우, 우수한 열적 안정성 및 캐리어 수송능(특히, 전자 수송능 및 발광능)을 기대할 수 있을 뿐만 아니라 소자의 구동전압, 효율, 수명 등이 향상될 수 있고, 높은 삼중항 에너지에 의해 최신 ETL 재료로서 TTF(triplet-triplet fusion) 효과로 인한 우수한 효율 상승을 나타낼 수 있다.Therefore, when the compound of the formula (1) of the present invention is used for an organic electroluminescent device, excellent thermal stability and carrier transport ability (in particular, electron transporting ability and light emitting ability) can be expected as well as driving voltage, Can be improved, and high triple-energetic energy can represent an excellent efficiency increase due to the triplet-triplet fusion (TTF) effect as the latest ETL material.
따라서, 본 발명의 화학식 1로 표시되는 화합물은 유기 전계 발광 소자의 유기물층인 정공 주입층, 정공 수송층, 발광층, 전자 수송층 및 전자 주입층 중 어느 하나의 재료로 사용될 수 있지만, 바람직하게는 발광층, 전자 수송층 및 전자 수송층에 추가로 적층되는 전자 수송 보조층 중 어느 하나의 재료, 보다 바람직하게는 전자 수송층, 또는 전자수송 보조층의 재료로 사용될 수 있다.Accordingly, the compound represented by the formula (1) of the present invention can be used as any one of a hole injection layer, a hole transporting layer, a light emitting layer, an electron transporting layer and an electron injecting layer which are organic compound layers of an organic electroluminescent device. Transporting layer and an electron transporting layer, and more preferably an electron transporting layer, or an electron transporting layer.
또한, 본 발명에 따른 화합물을 발광층 재료로 사용하는 경우, 구체적으로는 상기 화학식 1로 표시되는 화합물을 발광층의 인광 호스트, 형광 호스트 또는 도펀트 재료로 사용할 수 있으며, 바람직하게는 인광 호스트 재료로, 보다 바람직하게는 청색의 인광 호스트 재료로 사용할 수 있다.When the compound according to the present invention is used as a light emitting layer material, specifically, the compound represented by the above formula (1) can be used as a phosphorescent host, a fluorescent host or a dopant material of a light emitting layer, Preferably a blue phosphorescent host material.
또한, 본 발명에서 상기 유기 전계 발광 소자는 상기한 바와 같이 양극, 1층 이상의 유기물층 및 음극이 순차적으로 적층될 뿐만 아니라, 전극과 유기물층 계면에 절연층 또는 접착층을 추가로 포함할 수 있다. In addition, the organic electroluminescent device according to the present invention may further include an insulating layer or an adhesive layer at the interface between the electrode and the organic layer as well as the anode, one or more organic layers and the cathode sequentially laminated as described above.
본 발명의 유기 전계 발광 소자는 상기 유기물층 중 적어도 하나 이상(예컨대, 전자 수송 보조층)이 상기 화학식 1로 표시되는 화합물을 포함하도록 형성하는 것을 제외하고는, 당 기술 분야에 알려져 있는 재료 및 방법을 이용하여 다른 유기물층 및 전극을 형성하여 제조될 수 있다.The organic electroluminescent device of the present invention includes materials and methods known in the art, except that at least one or more of the organic material layers (for example, the electron transporting auxiliary layer) is formed to include the compound represented by Formula 1 To form another organic material layer and an electrode.
상기 유기물층은 진공 증착법이나 용액 도포법에 의하여 형성될 수 있다. 상기 용액 도포법의 예로는 스핀 코팅, 딥코팅, 닥터 블레이딩, 잉크젯 프린팅 또는 열 전사법 등이 있으나, 이에 한정되지 않는다.The organic material layer may be formed by a vacuum deposition method or a solution coating method. Examples of the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.
본 발명에서 사용 가능한 기판으로는 특별히 한정되지 않으며, 실리콘 웨이퍼, 석영, 유리판, 금속판, 플라스틱 필름 및 시트 등이 사용될 수 있다.The substrate usable in the present invention is not particularly limited, and a silicon wafer, quartz, a glass plate, a metal plate, a plastic film and a sheet can be used.
또, 양극 물질로는 예컨대 정공 주입이 원활하도록 일 함수가 높은 도전체로 만들어질 수 있으며, 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금; 아연산화물, 인듐산화물, 인듐 주석 산화물(ITO), 인듐 아연 산화물(IZO)과 같은 금속 산화물; ZnO:Al 또는 SnO2:Sb와 같은 금속과 산화물의 조합; 폴리티오펜, 폴리(3-메틸티오펜), 폴리[3,4-(에틸렌-1,2-디옥시)티오펜](PEDT), 폴리피롤 또는 폴리아닐린과 같은 전도성 고분자; 및 카본블랙 등이 있으나, 이에 한정되지는 않는다.The anode material may be made of a conductor having a high work function to facilitate injection of holes, for example, metals such as vanadium, chromium, copper, zinc, and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO 2: a combination of a metal and an oxide such as Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole or polyaniline; And carbon black, but are not limited thereto.
또, 음극 물질로는 예컨대 전자 주입이 원활하도록 일 함수가 낮은 도전체로 만들어질 수 있으며, 마그네슘, 칼슘, 나트륨, 칼륨, 타이타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄, 은, 주석, 또는 납과 같은 금속 또는 이들의 합금; 및 LiF/Al 또는 LiO2/Al과 같은 다층 구조 물질 등이 있으나, 이에 한정되지는 않는다.The negative electrode material may be made of a conductor having a low work function so as to facilitate electron injection and may be made of a material having a low work function such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, The same metal or an alloy thereof; And multi-layer structure materials such as LiF / Al or LiO 2 / Al, but are not limited thereto.
이하 본 발명을 실시예를 통하여 상세히 설명하면 다음과 같다. 단, 하기 실시예는 본 발명을 예시하는 것일 뿐, 본 발명이 하기 실시예에 의해 한정되는 것은 아니다.Hereinafter, the present invention will be described in detail with reference to examples. However, the following examples are illustrative of the present invention, and the present invention is not limited by the following examples.
[준비예 1] 2-브로모-[1,2,4]트리아졸로[1,5-a]피리딘의 합성[Preparation Example 1] Synthesis of 2-bromo- [1,2,4] triazolo [1,5-a] pyridine
<단계 1> [(2-피리디닐아미노)티옥소메틸]-, 에틸 에스터 (9CI)의 합성<Step 1> Synthesis of [(2-pyridinylamino) thioxomethyl] -, ethyl ester (9CI)
2-아미노피리딘 100 g (1.06 mol)에 디클로로메탄 500 mL를 가하였다. 0℃로 냉각하고 에톡시카보닐 이소티오시아네이트 139.3 g (1.06 mol)를 15분에 걸쳐 천천히 적가하였다. 반응액을 상온으로 올리고 20시간 교반하였다. 감압증류하여 용매를 적절히 제거하고 여과하였다. 훈풍 건조 후 목적 화합물 215 g (수율 90%)을 얻었다.To 100 g (1.06 mol) of 2-aminopyridine was added 500 mL of dichloromethane. Cooling to 0 < 0 > C and 139.3 g (1.06 mol) of ethoxycarbonyl isothiocyanate was slowly added dropwise over 15 minutes. The reaction solution was warmed to room temperature and stirred for 20 hours. The solvent was appropriately removed by distillation under reduced pressure and the mixture was filtered. After drying with warm air, 215 g of the objective compound (yield: 90%) was obtained.
<단계 2> [1,2,4]트리아졸로[1,5-a]피리딘-2-아민의 합성<Step 2> Synthesis of [1,2,4] triazolo [1,5-a] pyridin-2-amine
히드록실아민 히드로클로라이드 298 g (4.29 mol)에 EtOH/MeOH (1:1, 2.15 L) 혼합용매를 가하였다. 트리에틸아민 399 mL (2.86 mol)를 반응액에 가하고 1시간 교반하였다. [(2-피리디닐아미노)티옥소메틸]-, 에틸 에스터 (9CI) 215 g (0.95 mol)을 첨가하고 서서히 온도를 올려주어 3시간 동안 가열환류하였다. 온도를 상온으로 냉각하고 생성된 고체를 여과하였다. 얻어진 고체 생성물을 합하여 정제수, EtOH/MeOH 혼합용매 및 n-hexane으로 세척하고 훈풍 건조하여 목적 화합물 115 g (수율 90%)을 얻었다. A mixed solvent of EtOH / MeOH (1: 1, 2.15 L) was added to 298 g (4.29 mol) of hydroxylamine hydrochloride. 399 mL (2.86 mol) of triethylamine was added to the reaction solution, which was stirred for 1 hour. 215 g (0.95 mol) of [(2-pyridinylamino) thioxomethyl] -, ethyl ester (9CI) was added and the temperature was gradually raised, and the mixture was refluxed for 3 hours. The temperature was cooled to room temperature and the resulting solid was filtered. The resulting solid product was combined, washed with purified water, EtOH / MeOH mixed solvent and n-hexane, and dried under a warm air stream to obtain 115 g of the title compound (yield 90%).
1H-NMR (in DMSO) : δ 8.50 (dd, 1H), 7.39 (t, 1H), 7.29 (dd, 1H), 6.81 (t, 1H), 5.97 (s, 2H)(D, 1H), 6.97 (s, 2H), 7.90 (d, 1H)
[LCMS] : 134[LCMS]: 134
<단계 3> 2-브로모-[1,2,4]트리아졸로[1,5-a]피리딘의 합성<Step 3> Synthesis of 2-bromo- [1,2,4] triazolo [1,5-a] pyridine
[1,2,4]트리아졸로[1,5-a]피리딘-2-아민 115 g (0.86 mol)에 CuBr2 57.5 g (0.26 mol)과 THF 1.2 L를 가하였다. 반응액을 0℃로 냉각하고 HBr 1.2 L를 천천히 첨가하고 NaNO2 177 g (2.57 mol)을 정제수 600 mL에 용해시켜 천천히 적가하였다. 반응액을 상온에서 12시간 교반하였다. 반응액에 수산화나트륨수용액 500 mL 가하고 1 시간 교반 후 혼합액을 E.A 2 L로 추출한 후, 증류수로 세척하였다. 얻어진 유기층을 무수 MgSO4로 건조하고, 감압증류하고 실리카겔 컬럼크로마토그래피로 정제하여 목적 화합물 102 g (수율 60%)을 얻었다.57.5 g (0.26 mol) of CuBr 2 and 1.2 L of THF were added to 115 g (0.86 mol) of [1,2,4] triazolo [1,5-a] pyridin- The reaction solution was cooled to 0 ° C, 1.2 L of HBr was added slowly, and 177 g (2.57 mol) of NaNO 2 was dissolved in 600 mL of purified water and slowly added dropwise. The reaction solution was stirred at room temperature for 12 hours. 500 mL of an aqueous solution of sodium hydroxide was added to the reaction solution, and the mixture was stirred for 1 hour. Then, the mixture was extracted with 2 L of EA and washed with distilled water. The obtained organic layer was dried over anhydrous MgSO 4 , distilled under reduced pressure, and purified by silica gel column chromatography to obtain 102 g of the target compound (yield: 60%).
1H-NMR (in DMSO) : δ 8.92 (dd, 1H), 7.78 (dd, 1H), 7.72 (td, 1H), 7.23 (td, 1H)(Dd, 1H), 7.72 (td, 1H), 7.23 (td, 1H)
[LCMS] : 198[LCMS]: 198
[준비예 2] 2-브로모-8-페닐-[1,2,4]트리아졸로[1,5-a]피리딘의 합성[Preparation Example 2] Synthesis of 2-bromo-8-phenyl- [1,2,4] triazolo [1,5-a] pyridine
<단계 1> N-[[(3-브로모-2-피리디닐)아미노]티옥소메틸]-, 에틸 에스터의 합성Step 1 Synthesis of N - [[(3-bromo-2-pyridinyl) amino] thioxomethyl] -, ethyl ester
반응물로 2-아미노-3-브로모피리딘을 사용한 것을 제외하고는 [준비예 1]의 단계 1과 동일한 과정을 수행하여 목적 화합물 32 g (수율 88%)을 얻었다.The procedure of Step 1 of [Preparation Example 1] was repeated except for using 2-amino-3-bromopyridine as a reactant to obtain 32 g (yield: 88%) of the desired compound.
<단계 2> 8-브로모-[1,2,4]트리아졸로[1,5-a]피리딘-2-아민의 합성<Step 2> Synthesis of 8-bromo- [1,2,4] triazolo [1,5-a] pyridin-2-amine
반응물로 N-[[(3-브로모-2-피리디닐)아미노]티옥소메틸]-, 에틸 에스터를을 사용한 것을 제외하고는 [준비예 1]의 단계 2와 동일한 과정을 수행하여 목적 화합물 20.2 g (수율 90%)을 얻었다. The procedure of Step 2 of Preparation Example 1 was repeated except for using N - [[(3-bromo-2-pyridinyl) amino] thioxomethyl] - ethyl ester as a reactant, 20.2 g (yield 90%) was obtained.
1H-NMR (300Mz, CDCl3) : δ 8.54 (d, 1H), 7.69 (d, 1H), 6.77 (t, 1H), 6.22 (s, 2H) 1H-NMR (300Mz, CDCl 3 ): δ 8.54 (d, 1H), 7.69 (d, 1H), 6.77 (t, 1H), 6.22 (s, 2H)
[LCMS] : 213[LCMS]: 213
<단계 3> 2-브로모-[1,2,4]트리아졸로[1,5-a]피리딘의 합성<Step 3> Synthesis of 2-bromo- [1,2,4] triazolo [1,5-a] pyridine
8-브로모-[1,2,4]트리아졸로[1,5-a]피리딘-2-아민 20 g (93.9 mmol)과 페닐보로닉 산 13.7 g (113 mmol)에 dioxane 300 mL, H2O 100 mL를 가하였다. Pd(PPh3)4 5.4 g (4.7 mmol), K2CO3 38.9 g (282 mmol)을 첨가 후 120℃에서 3시간 가열환류하였다. 상온으로 온도를 냉각하고 반응액에 정제수 300 mL로 반응을 종결하였다. 혼합액을 E.A 500 mL로 추출한 후, 증류수로 세척하였다. 얻어진 유기층을 무수 MgSO4로 건조하고, 감압증류하고 실리카겔 컬럼크로마토그래피로 정제하여 목적 화합물 16.8 g (수율 85%)을 얻었다.To 20 g (93.9 mmol) of 8-bromo- [1,2,4] triazolo [1,5-a] pyridin-2-amine and 13.7 g (113 mmol) of phenylboronic acid were added 300 mL of dioxane, 2 O 100 mL was added. 5.4 g (4.7 mmol) of Pd (PPh 3 ) 4 and 38.9 g (282 mmol) of K 2 CO 3 were added, and the mixture was refluxed at 120 ° C. for 3 hours. The reaction mixture was cooled to room temperature and the reaction was terminated with 300 mL of purified water. The mixture was extracted with 500 mL of EA, and then washed with distilled water. The obtained organic layer was dried over anhydrous MgSO 4, distilled under reduced pressure, and purified by silica gel column chromatography to obtain the desired compound (16.8 g, yield 85%).
[LCMS] : 210[LCMS]: 210
<단계 4> 2-브로모-8-페닐-[1,2,4]트리아졸로[1,5-a]피리딘의 합성Step 4 Synthesis of 2-bromo-8-phenyl- [1,2,4] triazolo [1,5-a] pyridine
반응물로 2-브로모-[1,2,4]트리아졸로[1,5-a]피리딘을 사용한 것을 제외하고는 [준비예 1]의 단계 3과 동일한 과정을 수행하여 목적 화합물 14.2 g (수율 65%)을 얻었다. The procedure of Step 3 of [Preparation Example 1] was repeated except for using 2-bromo- [1,2,4] triazolo [1,5-a] pyridine as a reactant to obtain the title compound (14.2 g, 65%).
1H-NMR (in DMSO) : δ 8.92 (dd, 1H), 8.02 (m, 2H), 7.96 (dd, 1H), 7.52 (t, 2H), 7.46 (d, 1H), 7.33 (t, 1H) (D, 1H), 7.42 (d, 1H), 7.33 (t, 1H), 8.02 (m, 2H), 7.96
[LCMS] : 274[LCMS]: 274
[준비예 3] 2-브로모-6-페닐-[1,2,4]트리아졸로[1,5-a]피리딘의 합성[Preparation Example 3] Synthesis of 2-bromo-6-phenyl- [1,2,4] triazolo [1,5-a] pyridine
반응물로 2-아미노-5-브로모피리딘을 사용한 것을 제외하고는 [준비예 2]의 단계 1~4의 동일한 과정을 수행하여 목적 화합물 10.5 g (수율 38%)을 얻었다.The procedure of Steps 1 to 4 in [Preparation Example 2] was repeated except that 2-amino-5-bromopyridine was used as a reactant, to obtain 10.5 g (yield 38%) of the desired compound.
[LCMS] : 274[LCMS]: 274
[준비예 4] 2-브로모-6,8-디페닐-[1,2,4]트리아졸로[1,5-a]피리딘의 합성Preparation Example 4 Synthesis of 2-bromo-6,8-diphenyl- [1,2,4] triazolo [1,5-a] pyridine
<단계 1> [[(3,5-디클로로-2-피리디닐)아미노]티옥소메틸]-, 에틸 에스터 (9CI)의 합성<Step 1> Synthesis of [[(3,5-dichloro-2-pyridinyl) amino] thioxomethyl] -, ethyl ester (9CI)
반응물로 2-아미노-3,5-디클로로피리딘을 사용한 것을 제외하고는 [준비예 1]의 단계 1과 동일한 과정을 수행하여 목적 화합물 48 g (수율 92%)을 얻었다.The procedure of Step 1 of [Preparation Example 1] was repeated except for using 2-amino-3,5-dichloropyridine as a reactant to obtain 48 g of the title compound (yield 92%).
<단계 2> 6,8-디클로로-[1,2,4]트리아졸로[1,5-a]피리딘-2-아민의 합성Step 2 Synthesis of 6,8-dichloro- [1,2,4] triazolo [1,5-a] pyridin-2-amine
반응물로 [[(3,5-디클로로-2-피리디닐)아미노]티옥소메틸]-, 에틸 에스터 (9CI)을 사용한 것을 제외하고는 [준비예 1]의 단계 2와 동일한 과정을 수행하여 목적 화합물 29.8 g (수율 90%)을 얻었다. The same procedure as in Step 2 of [Preparation Example 1] was carried out except that [(3,5-dichloro-2-pyridinyl) amino] thioxomethyl] -, ethyl ester (9CI) 29.8 g (yield 90%) of the compound was obtained.
1H-NMR (300Mz, DMSO) : δ 8.88 (s, 1H), 7.77 (s, 1H), 6.36 (s, 2H)1H NMR (300 MHz, DMSO):? 8.88 (s, IH), 7.77 (s,
[LCMS] : 203[LCMS]: 203
<단계 3> 6,8-디페닐-[1,2,4]트리아졸로[1,5-a]피리딘-2-아민의 합성<Step 3> Synthesis of 6,8-diphenyl- [1,2,4] triazolo [1,5-a] pyridin-2-amine
6,8-디클로로-[1,2,4]트리아졸로[1,5-a]피리딘-2-아민 29 g (0.14 mol)과 페닐보로닉 산 41.8 g (0.34 mol)에 dioxane 400 mL, H2O 150 mL를 가하였다. Pd(OAc)2 3.2 g (0.014 mol), XPhos 13.6 g (0.0.09 mol), Cs2CO3 140 g (0.43 mol)을 첨가 후 120℃에서 3시간 가열환류하였다. 상온으로 온도를 냉각하고 반응액에 정제수 500 mL로 반응을 종결하였다. 혼합액을 E.A 1 L로 추출한 후, 증류수로 세척하였다. 얻어진 유기층을 무수 MgSO4로 건조하고, 감압증류하고 실리카겔 컬럼크로마토그래피로 정제하여 목적 화합물 35.6 g (수율 87%)을 얻었다.400 mL of dioxane was added to 29 g (0.14 mol) of 6,8-dichloro- [1,2,4] triazolo [1,5-a] pyridin- 150 mL of H 2 O was added. After adding 3.2 g (0.014 mol) of Pd (OAc) 2 , 13.6 g (0.0.09 mol) of XPhos and 140 g (0.43 mol) of Cs 2 CO 3 , the mixture was refluxed at 120 ° C for 3 hours. The reaction solution was cooled to room temperature and the reaction was terminated with 500 mL of purified water. The mixture was extracted with 1 L of EA, and then washed with distilled water. The obtained organic layer was dried over anhydrous MgSO 4 , distilled under reduced pressure, and purified by silica gel column chromatography to obtain the title compound (35.6 g, yield 87%).
1H-NMR (300Mz, CDCl3) : δ 8.49 (d, 1H), 7.95 (d, 2H), 7.76 (d, 1H), 7.59 (d, 2H), 7.49 (m, 4H), 7.42 (t, 2H), 4.60 (s, 2H) 1H-NMR (300Mz, CDCl 3 ): δ 8.49 (d, 1H), 7.95 (d, 2H), 7.76 (d, 1H), 7.59 (d, 2H), 7.49 (m, 4H), 7.42 (t, 2H), [delta] 4.60 (s, 2H)
[LCMS] : 286[LCMS]: 286
<단계 4> 2-브로모-6,8-디페닐-[1,2,4]트리아졸로[1,5-a]피리딘의 합성Step 4 Synthesis of 2-bromo-6,8-diphenyl- [1,2,4] triazolo [1,5-a] pyridine
반응물로 6,8-디페닐-[1,2,4]트리아졸로[1,5-a]피리딘-2-아민을 사용한 것을 제외하고는 [준비예 1]의 단계 3과 동일한 과정을 수행하여 목적 화합물 22.3 g (수율 52%)을 얻었다. The same procedure as in Step 3 of [Preparation Example 1] was carried out except that 6,8-diphenyl- [1,2,4] triazolo [1,5-a] pyridin- 22.3 g (yield 52%) of the desired compound was obtained.
1H-NMR (300Mz, CDCl3) : δ 8.66 (d, 1H), 8.00 (dd, 2H), 7.92 (d, 1H), 7.60 (d, 2H), 7.52 (m, 4H), 7.46 (d, 2H) 1H-NMR (300Mz, CDCl 3 ): δ 8.66 (d, 1H), 8.00 (dd, 2H), 7.92 (d, 1H), 7.60 (d, 2H), 7.52 (m, 4H), 7.46 (d, 2H)
[LCMS] : 350[LCMS]: 350
[준비예 5] 2-(4-(4-클로로나프탈렌-1-일)페닐)-[1,2,4]트리아졸로[1,5-a]피리딘의 합성Preparation Example 5 Synthesis of 2- (4- (4-chloronaphthalen-1-yl) phenyl) - [1,2,4] triazolo [1,5- a] pyridine
반응물로 준비예 1과 (4-(4-클로로나프탈렌-1-일)페닐)보로닉 산을 사용한 것을 제외하고는 [준비예 2]의 단계 3과 동일한 과정을 수행하여 목적 화합물 15.8 g (수율 63%)을 얻었다. The procedure of Step 3 of [Preparation Example 2] was repeated except for using (4- (4-chloronaphthalen-1-yl) phenyl) boronic acid as a reactant to obtain the desired compound (15.8 g, yield 63%).
[LCMS] : 355[LCMS]: 355
[준비예 6] 2-(4-(4-클로로나프탈렌-1-일)페닐)-[1,2,4]트리아졸로[1,5-a]피리딘의 합성Preparation Example 6 Synthesis of 2- (4- (4-chloronaphthalen-1-yl) phenyl) - [1,2,4] triazolo [1,5- a] pyridine
반응물로 준비예 1과 (3-(4-클로로나프탈렌-1-일)페닐)보로닉 산을 사용한 것을 제외하고는 [준비예 2]의 단계 3과 동일한 과정을 수행하여 목적 화합물 19.5 g (수율 58%)을 얻었다. The procedure of Step 3 of [Preparation Example 2] was repeated except for using (3- (4-chloronaphthalen-1-yl) phenyl) boronic acid as a reactant to obtain 19.5 g of the title compound 58%).
[LCMS] : 355[LCMS]: 355
[준비예 7] 2-(4-(5-클로로나프탈렌-1-일)페닐)-[1,2,4]트리아졸로[1,5-a]피리딘의 합성Preparation Example 7 Synthesis of 2- (4- (5-chloronaphthalen-1-yl) phenyl) - [1,2,4] triazolo [1,5- a] pyridine
반응물로 준비예 1과 (4-(5-클로로나프탈렌-1-일)페닐)보로닉 산을 사용한 것을 제외하고는 [준비예 2]의 단계 3과 동일한 과정을 수행하여 목적 화합물 19.5 g (수율 58%)을 얻었다. The procedure of Step 3 of [Preparation Example 2] was repeated except for using (4- (5-chloronaphthalen-1-yl) phenyl) boronic acid as a reactant to obtain 19.5 g of the desired compound 58%).
[LCMS] : 355[LCMS]: 355
[준비예 8] 2-(4-(5-클로로나프탈렌-1-일)페닐)-[1,2,4]트리아졸로[1,5-a]피리딘의 합성Preparation Example 8 Synthesis of 2- (4- (5-chloronaphthalen-1-yl) phenyl) - [1,2,4] triazolo [1,5- a] pyridine
반응물로 준비예 1과 (3-(5-클로로나프탈렌-1-일)페닐)보로닉 산을 사용한 것을 제외하고는 [준비예 2]의 단계 3과 동일한 과정을 수행하여 목적 화합물 25.5 g (수율 49%)을 얻었다. The procedure of Step 3 of [Preparation Example 2] was repeated except that Preparation Example 1 and (3- (5-chloronaphthalen-1-yl) phenyl) boronic acid were used as a reaction product to obtain 25.5 g 49%).
[LCMS] : 355[LCMS]: 355
[준비예 9] 2-(4-(6-클로로나프탈렌-2-일)페닐)-[1,2,4]트리아졸로[1,5-a]피리딘의 합성Preparation Example 9 Synthesis of 2- (4- (6-chloronaphthalen-2-yl) phenyl) - [1,2,4] triazolo [1,5- a] pyridine
반응물로 준비예 1과 (4-(6-클로로나프탈렌-2-일)페닐)보로닉 산을 사용한 것을 제외하고는 [준비예 2]의 단계 3과 동일한 과정을 수행하여 목적 화합물 14.2 g (수율 70%)을 얻었다. The procedure of Step 3 of [Preparation Example 2] was repeated except that Preparation Example 1 was used and (4- (6-chloronaphthalen-2-yl) phenyl) boronic acid was used as a reactant to obtain the title compound (14.2 g, 70%).
[LCMS] : 355[LCMS]: 355
[준비예 10] 2-(4-(7-클로로나프탈렌-2-일)페닐)-[1,2,4]트리아졸로[1,5-a]피리딘의 합성Preparation Example 10 Synthesis of 2- (4- (7-chloronaphthalen-2-yl) phenyl) - [1,2,4] triazolo [1,5- a] pyridine
반응물로 준비예 1과 (4-(7-클로로나프탈렌-2-일)페닐)보로닉 산을 사용한 것을 제외하고는 [준비예 2]의 단계 3과 동일한 과정을 수행하여 목적 화합물 17.5 g (수율 62%)을 얻었다. The procedure of Step 3 of [Preparation Example 2] was repeated except that Preparation Example 1 was used and (4- (7-chloronaphthalen-2-yl) phenyl) boronic acid was used as a reaction product to obtain 17.5 g 62%).
[LCMS] : 355[LCMS]: 355
[준비예 11] 2-(3-(7-클로로나프탈렌-2-일)페닐)-[1,2,4]트리아졸로[1,5-a]피리딘의 합성Preparation Example 11 Synthesis of 2- (3- (7-chloronaphthalen-2-yl) phenyl) - [1,2,4] triazolo [1,5- a] pyridine
반응물로 준비예 1과 (3-(7-클로로나프탈렌-2-일)페닐)보로닉 산을 사용한 것을 제외하고는 [준비예 2]의 단계 3과 동일한 과정을 수행하여 목적 화합물 17.5 g (수율 62%)을 얻었다. The procedure of Step 3 of [Preparation Example 2] was repeated except that Preparation Example 1 was used and (3- (7-chloronaphthalen-2-yl) phenyl) boronic acid was used as a reaction product to obtain 17.5 g 62%).
[LCMS] : 355[LCMS]: 355
[준비예 12] 2-(4-(4-클로로나프탈렌-1-일)페닐)-8-페닐-[1,2,4]트리아졸로[1,5-a]피리딘의 합성Preparation Example 12 Synthesis of 2- (4- (4-chloronaphthalen-1-yl) phenyl) -8-phenyl- [1,2,4] triazolo [1,5- a] pyridine
반응물로 준비예 2와 (4-(4-클로로나프탈렌-1-일)페닐)보로닉 산을 사용한 것을 제외하고는 [준비예 2]의 단계 3과 동일한 과정을 수행하여 목적 화합물 21.0 g (수율 55%)을 얻었다. The procedure of Step 3 of [Preparation Example 2] was repeated except for using Preparation Example 2 and (4- (4-chloronaphthalen-1-yl) phenyl) boronic acid as a reactant to obtain 21.0 g 55%).
[LCMS] : 431[LCMS]: 431
[준비예 13] 2-(3-(5-클로로나프탈렌-1-일)페닐)-8-페닐-[1,2,4]트리아졸로[1,5-a]피리딘의 합성Preparation Example 13 Synthesis of 2- (3- (5-chloronaphthalen-1-yl) phenyl) -8-phenyl- [1,2,4] triazolo [1,5- a] pyridine
반응물로 준비예 2와 (3-(5-클로로나프탈렌-1-일)페닐)보로닉 산을 사용한 것을 제외하고는 [준비예 2]의 단계 3과 동일한 과정을 수행하여 목적 화합물 18.2 g (수율 50%)을 얻었다. The procedure of Step 3 of [Preparation Example 2] was repeated except that in Preparation Example 2 and (3- (5-chloronaphthalen-1-yl) phenyl) boronic acid was used, 18.2 g of the title compound 50%).
[LCMS] : 431[LCMS]: 431
[준비예 14] 2-(3-(5-클로로나프탈렌-1-일)페닐)-8-페닐-[1,2,4]트리아졸로[1,5-a]피리딘의 합성Preparation Example 14 Synthesis of 2- (3- (5-chloronaphthalen-1-yl) phenyl) -8-phenyl- [1,2,4] triazolo [1,5- a] pyridine
반응물로 준비예 2와 2-(3-(6-클로로나프탈렌-2-일)페닐)-8-페닐-[1,2,4]트리아졸로[1,5-a]피리딘을 사용한 것을 제외하고는 [준비예 2]의 단계 3과 동일한 과정을 수행하여 목적 화합물 11.2 g (수율 72%)을 얻었다. Except that the reaction was carried out in the same manner as in Preparation Example 2 and using 2- (3- (6-chloronaphthalen-2-yl) phenyl) -8-phenyl- [1,2,4] triazolo [ Was subjected to the same procedure as in [Step 3] of [Preparation Example 2] to obtain the desired compound (11.2 g, yield 72%).
[LCMS] : 431[LCMS]: 431
[준비예 15] 2-(3-(7-클로로나프탈렌-2-일)페닐)-8-페닐-[1,2,4]트리아졸로[1,5-a]피리딘의 합성Preparation Example 15 Synthesis of 2- (3- (7-chloronaphthalen-2-yl) phenyl) -8-phenyl- [1,2,4] triazolo [1,5- a] pyridine
반응물로 준비예 2와 (3-(7-클로로나프탈렌-2-일)페닐)보로닉 산을 사용한 것을 제외하고는 [준비예 2]의 단계 3과 동일한 과정을 수행하여 목적 화합물 13.5 g (수율 49%)을 얻었다. The procedure of Step 3 of [Preparation Example 2] was repeated except that Preparation Example 2 and (3- (7-chloronaphthalen-2-yl) phenyl) boronic acid were used as reaction materials to obtain 13.5 g of the title compound 49%).
[LCMS] : 431[LCMS]: 431
[준비예 16] 2-(3-(4-클로로나프탈렌-1-일)페닐)-6-페닐-[1,2,4]트리아졸로[1,5-a]피리딘의 합성Preparation Example 16 Synthesis of 2- (3- (4-chloronaphthalen-1-yl) phenyl) -6-phenyl- [1,2,4] triazolo [1,5- a] pyridine
반응물로 준비예 3과 (3-(4-클로로나프탈렌-1-일)페닐)보로닉 산을 사용한 것을 제외하고는 [준비예 2]의 단계 3과 동일한 과정을 수행하여 목적 화합물 14.5 g (수율 60%)을 얻었다. Prepared in Example 3 and the reaction product (3- (4-chloro-1-yl) phenyl), and is [Preparation Example 2] Step 3 and by following the same procedure the desired compound 14.5 g (yield, except for using Nick Boro acid 60%).
[LCMS] : 431[LCMS]: 431
[준비예 17] 2-(4-(6-클로로나프탈렌-2-일)페닐)-6-페닐-[1,2,4]트리아졸로[1,5-a]피리딘의 합성Preparation Example 17 Synthesis of 2- (4- (6-chloronaphthalen-2-yl) phenyl) -6-phenyl- [l, 2,4] triazolo [1,5- a] pyridine
반응물로 준비예 3과 (4-(6-클로로나프탈렌-2-일)페닐)보로닉 산을 사용한 것을 제외하고는 [준비예 2]의 단계 3과 동일한 과정을 수행하여 목적 화합물 16.5 g (수율 58%)을 얻었다. The procedure of Step 3 of [Preparation Example 2] was repeated except that in Preparation Example 3 and (4- (6-chloronaphthalen-2-yl) phenyl) boronic acid was used, 16.5 g 58%).
[LCMS] : 431[LCMS]: 431
[준비예 18] 2-(3-(7-클로로나프탈렌-2-일)페닐)-6-페닐-[1,2,4]트리아졸로[1,5-a]피리딘의 합성[Preparation Example 18] Synthesis of 2- (3- (7-chloronaphthalen-2-yl) phenyl) -6- phenyl- [1,2,4] triazolo [1,5- a] pyridine
반응물로 준비예 3과 (3-(7-클로로나프탈렌-2-일)페닐)보로닉 산을 사용한 것을 제외하고는 [준비예 2]의 단계 3과 동일한 과정을 수행하여 목적 화합물 11.8 g (수율 49%)을 얻었다. The procedure of Step 3 of [Preparation Example 2] was repeated except that in Preparation Example 3 and (3- (7-chloronaphthalen-2-yl) phenyl) boronic acid was used, 11.8 g 49%).
[LCMS] : 431[LCMS]: 431
[준비예 19] 2-(4-(4-클로로나프탈렌-1-일)페닐)-6,8-디페닐-[1,2,4]트리아졸로[1,5-a]피리딘의 합성Preparation Example 19 Synthesis of 2- (4- (4-chloronaphthalen-1-yl) phenyl) -6,8-diphenyl- [1,2,4] triazolo [1,5- a] pyridine
반응물로 준비예 4와 (4-(4-클로로나프탈렌-1-일)페닐)보로닉 산을 사용한 것을 제외하고는 [준비예 2]의 단계 3과 동일한 과정을 수행하여 목적 화합물 20.4 g (수율 65%)을 얻었다. The procedure of Step 3 of [Preparation Example 2] was repeated except that in Preparation Example 4 and (4- (4-chloronaphthalen-1-yl) phenyl) boronic acid was used, 20.4 g 65%).
[LCMS] : 508[LCMS]: 508
[준비예 20] 2-(3-(5-클로로나프탈렌-1-일)페닐)-6,8-디페닐-[1,2,4]트리아졸로[1,5-a]피리딘의 합성Preparation Example 20 Synthesis of 2- (3- (5-chloronaphthalen-1-yl) phenyl) -6,8-diphenyl- [1,2,4] triazolo [1,5- a] pyridine
반응물로 준비예 4와 (3-(5-클로로나프탈렌-1-일)페닐)보로닉 산을 사용한 것을 제외하고는 [준비예 2]의 단계 3과 동일한 과정을 수행하여 목적 화합물 18.4 g (수율 70%)을 얻었다. The procedure of Step 3 of [Preparation Example 2] was repeated except that in Preparation Example 4 and (3- (5-chloronaphthalen-1-yl) phenyl) boronic acid was used, 18.4 g 70%).
[LCMS] : 508[LCMS]: 508
[준비예 21] 2-(4-(6-클로로나프탈렌-2-일)페닐)-6,8-디페닐-[1,2,4]트리아졸로[1,5-a]피리딘의 합성Preparation Example 21 Synthesis of 2- (4- (6-chloronaphthalen-2-yl) phenyl) -6,8-diphenyl- [1,2,4] triazolo [1,5- a] pyridine
반응물로 준비예 4와 (4-(6-클로로나프탈렌-2-일)페닐)보로닉 산을 사용한 것을 제외하고는 [준비예 2]의 단계 3과 동일한 과정을 수행하여 목적 화합물 15.5 g (수율 59%)을 얻었다. The procedure of Step 3 of [Preparation Example 2] was repeated except that Preparation Example 4 was used and (4- (6-chloronaphthalen-2-yl) phenyl) boronic acid was used as a reaction product to obtain 15.5 g 59%).
[LCMS] : 508[LCMS]: 508
[준비예 22] 2-(3-(4-클로로나프탈렌-1-일)페닐)-6,8-디페닐-[1,2,4]트리아졸로[1,5-a]피리딘의 합성Preparation Example 22 Synthesis of 2- (3- (4-chloronaphthalen-1-yl) phenyl) -6,8-diphenyl- [1,2,4] triazolo [1,5- a] pyridine
반응물로 준비예 4와 (4-(6-클로로나프탈렌-2-일)페닐)보로닉 산을 사용한 것을 제외하고는 [준비예 2]의 단계 3과 동일한 과정을 수행하여 목적 화합물 21.2 g (수율 70%)을 얻었다. The procedure of Step 3 of [Preparation Example 2] was repeated except that Preparation Example 4 was used and (4- (6-chloronaphthalen-2-yl) phenyl) boronic acid was used as a reaction product to obtain 21.2 g 70%).
[LCMS] : 508[LCMS]: 508
[준비예 23] 2-(4-(5-클로로나프탈렌-1-일)페닐)-6,8-디페닐-[1,2,4]트리아졸로[1,5-a]피리딘의 합성Preparation Example 23 Synthesis of 2- (4- (5-chloronaphthalen-1-yl) phenyl) -6,8-diphenyl- [1,2,4] triazolo [1,5- a] pyridine
반응물로 준비예 4와 (4-(5-클로로나프탈렌-1-일)페닐)보로닉 산을 사용한 것을 제외하고는 [준비예 2]의 단계 3과 동일한 과정을 수행하여 목적 화합물 13.4 g (수율 51%)을 얻었다. The procedure of Step 3 of [Preparation Example 2] was repeated except that in Preparation Example 4 and (4- (5-chloronaphthalen-1-yl) phenyl) boronic acid was used, 13.4 g 51%).
[LCMS] : 508[LCMS]: 508
[합성예 1] 화합물 2의 합성[Synthesis Example 1] Synthesis of Compound 2
반응물로 준비예 5의 2-(4-(4-클로로나프탈렌-1-일)페닐)-[1,2,4]트리아졸로[1,5-a]피리딘과 (4'-시아노-[1,1'-비페닐]-4-일)보로닉 산을 사용한 것을 제외하고는 [준비예 4]의 단계 3과 동일한 과정을 수행하여 목적 화합물 5.5 g (수율 40%)을 얻었다. The reaction was carried out in the same manner as in Example 5 using 2- (4- (4-chloronaphthalen-1-yl) phenyl) - [1,2,4] triazolo [ The procedure of Step 3 of [Preparation Example 4] was repeated except for using 1,1'-biphenyl] -4-yl) boronic acid to obtain the title compound (5.5 g, yield 40%).
[LCMS] : 498[LCMS]: 498
[합성예 2] 화합물 5의 합성[Synthesis Example 2] Synthesis of Compound 5
반응물로 준비예 6의 2-(3-(4-클로로나프탈렌-1-일)페닐)-[1,2,4]트리아졸로[1,5-a]피리딘과 (4'-시아노-[1,1'-비페닐]-3-일)보로닉 산을 사용한 것을 제외하고는 [준비예 4]의 단계 3과 동일한 과정을 수행하여 목적 화합물 6.0 g (수율 47%)을 얻었다.Example 6 Preparation of a reaction product of 2- (3- (4-chloro-1-yl) phenyl) - [l, 2,4] triazolo [1,5-a] pyridine and (4'-cyano- [ The procedure of Step 3 of [Preparation Example 4] was repeated except for using 1,1'-biphenyl] -3-yl) boronic acid to obtain 6.0 g (yield 47%) of the target compound.
[LCMS] : 498[LCMS]: 498
[합성예 3] 화합물 7의 합성[Synthesis Example 3] Synthesis of Compound 7
반응물로 준비예 5의 2-(4-(4-클로로나프탈렌-1-일)페닐)-[1,2,4]트리아졸로[1,5-a]피리딘과 (3',5'-디시아노-[1,1'-비페닐]-4-일)보로닉 산을 사용한 것을 제외하고는 [준비예 4]의 단계 3과 동일한 과정을 수행하여 목적 화합물 3.8 g (수율 65%)을 얻었다. To a reaction mixture were added 2- (4- (4-chloronaphthalen-1-yl) phenyl) - [1,2,4] triazolo [1,5- a] pyridine prepared in Preparation Example 5 and (3 ', 5'- (Yield: 65%) was obtained by carrying out the same procedure as in [Step 3] of [Preparation Example 4], except that [- (4-fluoro-phenoxy) .
[LCMS] : 523[LCMS]: 523
[합성예 4] 화합물 12의 합성[Synthesis Example 4] Synthesis of Compound 12
반응물로 준비예 7의 2-(4-(5-클로로나프탈렌-1-일)페닐)-[1,2,4]트리아졸로[1,5-a]피리딘과 (4'-시아노-[1,1'-비페닐]-4-일)보로닉 산을 사용한 것을 제외하고는 [준비예 4]의 단계 3과 동일한 과정을 수행하여 목적 화합물 6.2 g (수율 58%)을 얻었다. A mixture of 2- (4- (5-chloronaphthalen-1-yl) phenyl) - [1,2,4] triazolo [1,5- a] pyridine prepared in Preparation Example 7 and (4'- The procedure of Step 3 of [Preparation Example 4] was repeated except for using 1,1'-biphenyl] -4-yl) boronic acid to obtain 6.2 g of the desired compound (yield: 58%).
[LCMS] : 498[LCMS]: 498
[합성예 5] 화합물 18의 합성[Synthesis Example 5] Synthesis of Compound 18
반응물로 준비예 8의 2-(3-(5-클로로나프탈렌-1-일)페닐)-[1,2,4]트리아졸로[1,5-a]피리딘과 (3,5-디시아노페닐)보로닉 산을 사용한 것을 제외하고는 [준비예 4]의 단계 3과 동일한 과정을 수행하여 목적 화합물 4.9 g (수율 60%)을 얻었다. To a reaction mixture were added 2- (3- (5-chloronaphthalen-1-yl) phenyl) - [1,2,4] triazolo [1,5- a] pyridine prepared in Preparation 8 and (3,5- ) Boronic acid as starting materials, the procedure of Step 3 of [Preparation Example 4] was repeated to obtain 4.9 g (yield: 60%) of the desired compound.
[LCMS] : 447[LCMS]: 447
[합성예 6] 화합물 22의 합성[Synthesis Example 6] Synthesis of Compound 22
반응물로 준비예 9의 2-(4-(6-클로로나프탈렌-2-일)페닐)-[1,2,4]트리아졸로[1,5-a]피리딘과 (4'-시아노-[1,1'-비페닐]-4-일)보로닉 산을 사용한 것을 제외하고는 [준비예 4]의 단계 3과 동일한 과정을 수행하여 목적 화합물 3.1 g (수율 52%)을 얻었다. The reaction was carried out in the same manner as in Example 9 using 2- (4- (6-chloronaphthalen-2-yl) phenyl) - [1,2,4] triazolo [ The procedure of Step 3 of [Preparation Example 4] was repeated except for using 1,1'-biphenyl] -4-yl) boronic acid to obtain 3.1 g of the desired compound (yield 52%).
[LCMS] : 498[LCMS]: 498
[합성예 7] 화합물 32의 합성[Synthesis Example 7] Synthesis of Compound 32
반응물로 준비예 10의 2-(4-(7-클로로나프탈렌-2-일)페닐)-[1,2,4]트리아졸로[1,5-a]피리딘과 (4'-시아노-[1,1'-비페닐]-4-일)보로닉 산을 사용한 것을 제외하고는 [준비예 4]의 단계 3과 동일한 과정을 수행하여 목적 화합물 4.4 g (수율 55%)을 얻었다. The reaction was carried out in the same manner as in Example 10 using 2- (4- (7-chloronaphthalen-2-yl) phenyl) - [1,2,4] triazolo [ The procedure of Step 3 of [Preparation Example 4] was repeated except for using 1,1'-biphenyl] -4-yl) boronic acid to obtain the desired compound (4.4 g, yield 55%).
[LCMS] : 498[LCMS]: 498
[합성예 8] 화합물 40의 합성[Synthesis Example 8] Synthesis of Compound 40
반응물로 준비예 11의 2-(3-(7-클로로나프탈렌-2-일)페닐)-[1,2,4]트리아졸로[1,5-a]피리딘과 (3',5'-디시아노-[1,1'-비페닐]-3-일)보로닉 산을 사용한 것을 제외하고는 [준비예 4]의 단계 3과 동일한 과정을 수행하여 목적 화합물 2.7 g (수율 64%)을 얻었다. The reaction was carried out in the same manner as in Example 11 using 2- (3- (7-chloronaphthalen-2-yl) phenyl) - [1,2,4] triazolo [ (Yield: 64%) was obtained by carrying out the same procedure as in [Step 3] of [Preparation Example 4], except for using [3- .
[LCMS] : 523[LCMS]: 523
[합성예 9] 화합물 42의 합성[Synthesis Example 9] Synthesis of Compound 42
반응물로 준비예 12의 2-(4-(4-클로로나프탈렌-1-일)페닐)-8-페닐-[1,2,4]트리아졸로[1,5-a]피리딘과 (4'-시아노-[1,1'-비페닐]-4-일)보로닉 산을 사용한 것을 제외하고는 [준비예 4]의 단계 3과 동일한 과정을 수행하여 목적 화합물 5.1 g (수율 48%)을 얻었다. Phenyl- [l, 2,4] triazolo [l, 5-a] pyridine prepared in Preparation Example 12 and (4'-chloro- The procedure of Step 3 of [Preparation Example 4] was repeated except for using cyano- [1,1'-biphenyl] -4-yl) boronic acid to obtain 5.1 g (yield 48%) of the desired compound .
[LCMS] : 574[LCMS]: 574
[합성예 10] 화합물 53의 합성[Synthesis Example 10] Synthesis of Compound 53
반응물로 준비예 13의 2-(3-(5-클로로나프탈렌-1-일)페닐)-8-페닐-[1,2,4]트리아졸로[1,5-a]피리딘과 (4-시아노페닐)보로닉 산을 사용한 것을 제외하고는 [준비예 4]의 단계 3과 동일한 과정을 수행하여 목적 화합물 4.5 g (수율 52%)을 얻었다. Phenyl] - [1,2,4] triazolo [1,5-a] pyridine prepared in Preparation Example 13 and (4-cyanophenyl) Naphthyl) boronic acid was used in place of 4-chloro-4-fluorobenzaldehyde, the procedure of Step 3 of [Preparation Example 4] was repeated to obtain the desired compound (4.5 g, yield 52%).
[LCMS] : 498[LCMS]: 498
[합성예 11] 화합물 65의 합성[Synthesis Example 11] Synthesis of Compound 65
반응물로 준비예 14의 2-(3-(6-클로로나프탈렌-2-일)페닐)-8-페닐-[1,2,4]트리아졸로[1,5-a]피리딘과 (4'-시아노-[1,1'-비페닐]-3-일)보로닉 산을 사용한 것을 제외하고는 [준비예 4]의 단계 3과 동일한 과정을 수행하여 목적 화합물 8.2 g (수율 65%)을 얻었다. Phenyl] - [1,2,4] triazolo [1,5-a] pyridine prepared in Preparation Example 14 and (4'- The procedure of Step 3 of [Preparation Example 4] was repeated except for using cyano- [1,1'-biphenyl] -3-yl) boronic acid to obtain 8.2 g (yield 65%) of the desired compound .
[LCMS] : 574[LCMS]: 574
[합성예 12] 화합물 70의 합성[Synthesis Example 12] Synthesis of Compound 70
반응물로 준비예 14의 2-(3-(6-클로로나프탈렌-2-일)페닐)-8-페닐-[1,2,4]트리아졸로[1,5-a]피리딘과 (3',5'-디시아노-[1,1'-비페닐]-3-일)보로닉 산을 사용한 것을 제외하고는 [준비예 4]의 단계 3과 동일한 과정을 수행하여 목적 화합물 7.2 g (수율 57%)을 얻었다. Phenyl] - [l, 2,4] triazolo [l, 5-a] pyridine prepared in Preparation Example 14 and (3 ' The procedure of Step 3 of [Preparation Example 4] was repeated except for using 5'-dicyano- [1,1'-biphenyl] -3-yl) boronic acid to obtain 7.2 g of the title compound %).
[LCMS] : 599[LCMS]: 599
[합성예 13] 화합물 75의 합성[Synthesis Example 13] Synthesis of Compound 75
반응물로 준비예 15의 2-(3-(7-클로로나프탈렌-2-일)페닐)-8-페닐-[1,2,4]트리아졸로[1,5-a]피리딘과 (4'-시아노-[1,1'-비페닐]-3-일)보로닉 산을 사용한 것을 제외하고는 [준비예 4]의 단계 3과 동일한 과정을 수행하여 목적 화합물 5.0 g (수율 63%)을 얻었다. Phenyl] - [1,2,4] triazolo [1,5-a] pyridine prepared in Preparative Example 15 and (4'-tert-butyldicyclohexylcarbodiimide) (Yield: 63%) was obtained by carrying out the same procedure as in [Step 3] of [Preparation Example 4], except that cyano- [1,1'-biphenyl] -3- .
[LCMS] : 574[LCMS]: 574
[합성예 14] 화합물 84의 합성[Synthesis Example 14] Synthesis of Compound 84
반응물로 준비예 16의 2-(3-(4-클로로나프탈렌-1-일)페닐)-6-페닐-[1,2,4]트리아졸로[1,5-a]피리딘과 (4'-시아노-[1,1'-비페닐]-4-일)보로닉 산을 사용한 것을 제외하고는 [준비예 4]의 단계 3과 동일한 과정을 수행하여 목적 화합물 3.3 g (수율 69%)을 얻었다. Phenyl] - [l, 2,4] triazolo [l, 5-a] pyridine prepared in Preparation Example 16 and (4'- The procedure of Step 3 of [Preparation Example 4] was repeated except for using cyano- [1,1'-biphenyl] -4-yl) boronic acid to obtain 3.3 g of the desired compound (yield 69%) .
[LCMS] : 574[LCMS]: 574
[합성예 15] 화합물 90의 합성[Synthesis Example 15] Synthesis of Compound 90
반응물로 준비예 16의 2-(3-(4-클로로나프탈렌-1-일)페닐)-6-페닐-[1,2,4]트리아졸로[1,5-a]피리딘과 (3',5'-디시아노-[1,1'-비페닐]-3-일)보로닉 산을 사용한 것을 제외하고는 [준비예 4]의 단계 3과 동일한 과정을 수행하여 목적 화합물 4.1 g (수율 55%)을 얻었다. The reaction was carried out in the same manner as in Example 16 using 2- (3- (4-chloronaphthalen-1-yl) phenyl) -6-phenyl- The procedure of Step 3 of [Preparation Example 4] was repeated except for using 5'-dicyano- [1,1'-biphenyl] -3-yl) boronic acid to obtain 4.1 g of the desired compound %).
[LCMS] : 599[LCMS]: 599
[합성예 16] 화합물 102의 합성[Synthesis Example 16] Synthesis of Compound 102
반응물로 준비예 17의 2-(4-(6-클로로나프탈렌-2-일)페닐)-6-페닐-[1,2,4]트리아졸로[1,5-a]피리딘과 (4'-시아노-[1,1'-비페닐]-4-일)보로닉 산을 사용한 것을 제외하고는 [준비예 4]의 단계 3과 동일한 과정을 수행하여 목적 화합물 7.1 g (수율 62%)을 얻었다. Phenyl] - [1,2,4] triazolo [1,5-a] pyridine prepared in Preparative Example 17 and (4'-chloro- The procedure of Step 3 of [Preparation Example 4] was repeated except for using cyano- [1,1'-biphenyl] -4-yl) boronic acid to obtain 7.1 g of the desired compound (yield 62%) .
[LCMS] : 574[LCMS]: 574
[합성예 17] 화합물 113의 합성[Synthesis Example 17] Synthesis of Compound 113
반응물로 준비예 18의 2-(3-(7-클로로나프탈렌-2-일)페닐)-6-페닐-[1,2,4]트리아졸로[1,5-a]피리딘과 (4-시아노페닐)보로닉 산을 사용한 것을 제외하고는 [준비예 4]의 단계 3과 동일한 과정을 수행하여 목적 화합물 5.5 g (수율 49%)을 얻었다. Phenyl] - [l, 2,4] triazolo [l, 5-a] pyridine prepared in Preparation Example 18 and (4-cyanophenyl) Naphthyl) boronic acid, the procedure of Step 3 of [Preparation Example 4] was repeated to obtain the desired compound (5.5 g, yield 49%).
[LCMS] : 498[LCMS]: 498
[합성예 18] 화합물 119의 합성[Synthesis Example 18] Synthesis of Compound 119
반응물로 준비예 18의 2-(3-(7-클로로나프탈렌-2-일)페닐)-6-페닐-[1,2,4]트리아졸로[1,5-a]피리딘과 (3',5'-디시아노-[1,1'-비페닐]-4-일)보로닉 산을 사용한 것을 제외하고는 [준비예 4]의 단계 3과 동일한 과정을 수행하여 목적 화합물 4.8 g (수율 58%)을 얻었다. Phenyl] - [l, 2,4] triazolo [l, 5-a] pyridine prepared in Preparation Example 18 and (3 ' The procedure of Step 3 of [Preparation Example 4] was repeated except for using 5'-dicyano- [1,1'-biphenyl] -4-yl) boronic acid to obtain 4.8 g (yield: 58% %).
[LCMS] : 599[LCMS]: 599
[합성예 19] 화합물 122의 합성[Synthesis Example 19] Synthesis of Compound 122
반응물로 준비예 19의 2-(4-(4-클로로나프탈렌-1-일)페닐)-6,8-디페닐-[1,2,4]트리아졸로[1,5-a]피리딘과 (4'-시아노-[1,1'-비페닐]-4-일)보로닉 산을 사용한 것을 제외하고는 [준비예 4]의 단계 3과 동일한 과정을 수행하여 목적 화합물 5.3 g (수율 40%)을 얻었다. Preparation of Example 19 by reaction of 2- (4- (4-chloro-1-yl) phenyl) - 6, 8-diphenyl- [1,2,4] triazolo [1,5-a] pyridine and ( The procedure of Step 3 of [Preparation Example 4] was repeated except for using 4'-cyano- [1,1'-biphenyl] -4-yl) boronic acid to obtain 5.3 g of the desired compound %).
[LCMS] : 650[LCMS]: 650
[합성예 20] 화합물 127의 합성[Synthesis Example 20] Synthesis of Compound 127
반응물로 준비예 19의 2-(4-(4-클로로나프탈렌-1-일)페닐)-6,8-디페닐-[1,2,4]트리아졸로[1,5-a]피리딘과 (3',5'-디시아노-[1,1'-비페닐]-4-일)보로닉 산을 사용한 것을 제외하고는 [준비예 4]의 단계 3과 동일한 과정을 수행하여 목적 화합물 5.0 g (수율 45%)을 얻었다. Preparation of Example 19 by reaction of 2- (4- (4-chloro-1-yl) phenyl) - 6, 8-diphenyl- [1,2,4] triazolo [1,5-a] pyridine and ( The procedure of Step 3 of [Preparation Example 4] was repeated except for using 3 ', 5'-dicyano- [1,1'-biphenyl] -4-yl) boronic acid to obtain 5.0 g (Yield: 45%).
[LCMS] : 650[LCMS]: 650
[합성예 21] 화합물 133의 합성[Synthesis Example 21] Synthesis of Compound 133
반응물로 준비예 20의 2-(3-(5-클로로나프탈렌-1-일)페닐)-6,8-디페닐-[1,2,4]트리아졸로[1,5-a]피리딘과 (4-시아노페닐)보로닉 산을 사용한 것을 제외하고는 [준비예 4]의 단계 3과 동일한 과정을 수행하여 목적 화합물 6.6 g (수율 52%)을 얻었다. Preparation of Example 20 by reaction of 2- (3- (5-chloro-1-yl) phenyl) - 6, 8-diphenyl- [1,2,4] triazolo [1,5-a] pyridine and ( The procedure of Step 3 of [Preparation Example 4] was repeated except for using 4-cyanophenyl) boronic acid to obtain the desired compound (6.6 g, yield 52%).
[LCMS] : 574[LCMS]: 574
[합성예 22] 화합물 142의 합성[Synthesis Example 22] Synthesis of Compound 142
반응물로 준비예 21의 2-(4-(6-클로로나프탈렌-2-일)페닐)-6,8-디페닐-[1,2,4]트리아졸로[1,5-a]피리딘과 (4'-시아노-[1,1'-비페닐]-4-일)보로닉 산을 사용한 것을 제외하고는 [준비예 4]의 단계 3과 동일한 과정을 수행하여 목적 화합물 3.5 g (수율 68%)을 얻었다. Prepared by reaction of Example 21, 2- (4- (6-chloronaphthalene-2-yl) phenyl) - 6, 8-diphenyl- [1,2,4] triazolo [1,5-a] pyridine and ( The procedure of Step 3 of [Preparation Example 4] was repeated except for using 4'-cyano- [1,1'-biphenyl] -4-yl) boronic acid to obtain 3.5 g of the desired compound %).
[LCMS] : 650[LCMS]: 650
[합성예 23] 화합물 165의 합성[Synthesis Example 23] Synthesis of Compound 165
반응물로 준비예 22의 2-(3-(4-클로로나프탈렌-1-일)페닐)-6,8-디페닐-[1,2,4]트리아졸로[1,5-a]피리딘과 (3'-시아노-[1,1'-비페닐]-3-일)보로닉 산을 사용한 것을 제외하고는 [준비예 4]의 단계 3과 동일한 과정을 수행하여 목적 화합물 4.1 g (수율 58%)을 얻었다. Prepared by reaction of Example 22, 2- (4- (4-chloro-1-yl) phenyl) - 6, 8-diphenyl- [1,2,4] triazolo [1,5-a] pyridine and ( The procedure of Step 3 of [Preparation Example 4] was repeated except for using 3'-cyano- [1,1'-biphenyl] -3-yl) boronic acid to obtain 4.1 g of the title compound %).
[LCMS] : 650[LCMS]: 650
[합성예 24] 화합물 167의 합성[Synthesis Example 24] Synthesis of Compound 167
반응물로 준비예 23의 2-(4-(5-클로로나프탈렌-1-일)페닐)-6,8-디페닐-[1,2,4]트리아졸로[1,5-a]피리딘과 (3'-시아노-[1,1'-비페닐]-4-일)보로닉 산을 사용한 것을 제외하고는 [준비예 4]의 단계 3과 동일한 과정을 수행하여 목적 화합물 3.3 g (수율 62%)을 얻었다. Prepared by reaction of Example 23, 2- (4- (5-chloro-1-yl) phenyl) - 6, 8-diphenyl- [1,2,4] triazolo [1,5-a] pyridine and ( The procedure of Step 3 of [Preparation Example 4] was repeated except for using 3'-cyano- [1,1'-biphenyl] -4-yl) boronic acid to obtain 3.3 g of the target compound %).
[실시예 1] 청색 유기 전계 발광 소자의 제조[Example 1] Production of blue organic electroluminescent device
합성예 1에서 합성된 화합물 2를 통상적으로 알려진 방법으로 고순도 승화정제를 한 후, 하기와 같이 청색 유기 전계 발광 소자를 제조하였다.Compound 2 synthesized in Synthesis Example 1 was subjected to high purity sublimation purification by a conventionally known method, and blue organic electroluminescent devices were prepared as follows.
ITO (Indium tin oxide)가 1500 Å 두께로 박막 코팅된 유리 기판을 증류수 초음파로 세척하였다. 증류수 세척이 끝나면, 이소프로필 알코올, 아세톤, 메탄올 등의 용제로 초음파 세척을 하고, 건조시킨 후, UV OZONE 세정기(Power sonic 405, 화신테크)로 이송시킨 다음, UV를 이용하여 상기 기판을 5분간 세정하고 진공 증착기로 기판을 이송하였다.Glass substrate coated with ITO (Indium tin oxide) thin film with thickness of 1500 Å was washed with distilled water ultrasonic wave. After the distilled water was washed, it was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, dried, transferred to a UV OZONE cleaner (Power sonic 405, Hoshin Tech) And the substrate was transferred to a vacuum evaporator.
상기와 같이 준비된 ITO 투명 전극 위에, DS-205 (80 nm) / NPB (15 nm) / ADN + 5 % DS-405 (30nm) / 화합물 2 (30 nm)/ LiF (1 nm)/ Al (200 nm) 순으로 적층하여 유기 전계 발광 소자를 제조하였다.(80 nm) / NPB (15 nm) / ADN + 5% DS-405 (30 nm) / Compound 2 (30 nm) / LiF (1 nm) / Al (200 nm) on the ITO transparent electrode prepared above. nm) were stacked in this order to produce an organic electroluminescent device.
이때 사용된 NPB, ADN 및 Alq3의 구조는 다음과 같다.The structures of NPB, ADN and Alq 3 used in this case are as follows.
[실시예 2] ~ [실시예 13] 청색 유기 전계 발광 소자의 제조[Example 2] - [Example 13] Production of blue organic electroluminescent device
실시예 1에서 사용된 화합물 2 대신 하기 표 1에 기재된 화합물을 각각 전자수송층 물질로 사용하는 것을 제외하고는, 실시예 1와 동일하게 수행하여 청색 유기 전계 발광 소자를 제조하였다.A blue organic electroluminescent device was fabricated in the same manner as in Example 1 except that the compound shown in Table 1 was used as the electron transport layer material instead of the compound 2 used in Example 1.
[비교예 1] 청색 유기 전계 발광 소자의 제조[Comparative Example 1] Production of blue organic electroluminescent device
전자 수송층 물질인 Alq3을 30nm로 증착하는 것을 제외하고는, 실시예 1과 동일하게 수행하여 청색 유기 전계 발광 소자를 제작하였다. A blue organic electroluminescent device was fabricated in the same manner as in Example 1, except that Alq 3 , which is an electron transporting layer material, was deposited at a thickness of 30 nm.
[평가예 1][Evaluation Example 1]
실시예 1 내지 13 및 비교예 1에서 각각 제조된 유기 전계 발광 소자에 대하여, 전류밀도 10 mA/㎠에서의 구동전압, 전류효율, 발광파장을 측정하였고, 그 결과를 하기 표 1에 나타내었다.The driving voltage, current efficiency, and emission wavelength at the current density of 10 mA / cm 2 were measured for the organic electroluminescent devices manufactured in Examples 1 to 13 and Comparative Example 1, respectively, and the results are shown in Table 1 below.
| 샘플Sample | 전자수송층Electron transport layer | 구동전압(V)The driving voltage (V) | 발광피크(nm)Emission peak (nm) | 전류효율(cd/A)Current efficiency (cd / A) |
| 실시예 1Example 1 | 화합물 2Compound 2 | 3.83.8 | 452452 | 8.88.8 |
| 실시예 2Example 2 | 화합물 7Compound 7 | 3.93.9 | 453453 | 8.58.5 |
| 실시예 3Example 3 | 화합물 12Compound 12 | 4.14.1 | 450450 | 9.09.0 |
| 실시예 4Example 4 | 화합물 22Compound 22 | 4.24.2 | 452452 | 8.58.5 |
| 실시예 5Example 5 |
화합물 32 |
3.53.5 | 452452 | 8.18.1 |
| 실시예 6Example 6 | 화합물 42Compound 42 | 3.43.4 | 453453 | 8.98.9 |
| 실시예 7Example 7 | 화합물 70Compound 70 | 3.63.6 | 450450 | 8.28.2 |
| 실시예 8Example 8 | 화합물 75Compound 75 | 4.04.0 | 450450 | 8.28.2 |
| 실시예 9Example 9 | 화합물 102Compound 102 | 3.83.8 | 451451 | 8.98.9 |
| 실시예 10Example 10 | 화합물 119Compound 119 | 3.33.3 | 452452 | 9.19.1 |
| 실시예 11Example 11 | 화합물 127Compound 127 | 3.43.4 | 451451 | 8.88.8 |
| 실시예 12Example 12 | 화합물 142Compound 142 | 3.83.8 | 452452 | 8.98.9 |
| 실시예 13Example 13 | 화합물 167Compound 167 | 3.53.5 | 450450 | 8.58.5 |
| 비교예 1Comparative Example 1 | Alq3 Alq 3 | 4.84.8 | 457457 | 5.85.8 |
[실시예 14] 청색 유기 전계 발광 소자의 제조[Example 14] Production of blue organic electroluminescent device
합성예 1에서 합성된 화합물 5를 통상적으로 알려진 방법으로 고순도 승화정제를 한 후, 아래의 과정에 따라 청색 유기 전계 발광 소자를 제작하였다.Compound 5 synthesized in Synthesis Example 1 was subjected to high purity sublimation purification by a conventionally known method, and a blue organic electroluminescent device was fabricated according to the following procedure.
ITO (Indium tin oxide)가 1500 Å 두께로 박막 코팅된 유리 기판을 증류수 초음파로 세척하였다. 증류수 세척이 끝나면, 이소프로필 알코올, 아세톤, 메탄올 등의 용제로 초음파 세척을 하고 건조시킨 후, UV OZONE 세정기(Power sonic 405, 화신테크)로 이송시킨 다음, UV를 이용하여 상기 기판을 5분간 세정하고 진공 증착기로 기판을 이송하였다.Glass substrate coated with ITO (Indium tin oxide) thin film with thickness of 1500 Å was washed with distilled water ultrasonic wave. After the distilled water was washed, the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, and dried. Then, the substrate was transferred to a UV OZONE cleaner (Power sonic 405, Hoshin Tech) And the substrate was transferred to a vacuum evaporator.
상기와 같이 준비된 ITO 투명 전극 위에, DS-205 (80 nm) / NPB (15 nm) / ADN + 5 % DS-405 (㈜두산전자, 30nm) / 화합물 5 (5 nm) / Alq3 (25 nm) / LiF (1 nm) / Al (200 nm) 순으로 적층하여 유기 전계 발광 소자를 제조하였다.DS-205 (80 nm) / NPB (15 nm) / ADN + 5% DS-405 (Doosan Electronics, 30 nm) / Compound 5 (5 nm) / Alq 3 ) / LiF (1 nm) / Al (200 nm) were stacked in this order to fabricate an organic electroluminescent device.
이때 사용된 NPB, ADN 및 Alq3의 구조는 다음과 같다.The structures of NPB, ADN and Alq 3 used in this case are as follows.
[실시예 15] ~ [실시예 24] 청색 유기 전계 발광 소자의 제조[Example 15] - [Example 24] Production of blue organic electroluminescent device
실시예 14에서 사용된 화합물 5 대신 하기 표 2에 기재된 화합물을 각각 전자수송보조층 물질로 사용하는 것을 제외하고는, 실시예 14와 동일하게 수행하여 청색 유기 전계 발광 소자를 제조하였다.A blue organic electroluminescent device was fabricated in the same manner as in Example 14, except that the compound shown in Table 2 was used instead of the compound 5 used in Example 14 as an electron transporting auxiliary layer material.
[비교예 2] 청색 유기 전계 발광 소자의 제조[Comparative Example 2] Production of blue organic electroluminescent device
실시예 14에서 전자수송보조층 물질로 사용된 화합물 5를 사용하지 않고, 전자 수송층 물질인 Alq3를 25 nm 대신 30 nm로 증착하는 것을 제외하고는, 실시예 14와 동일하게 수행하여 청색 유기 전계 발광 소자를 제작하였다. The procedure of Example 14 was repeated except that the compound 5 used as the electron transporting auxiliary layer material in Example 14 was not used and the electron transporting layer material Alq 3 was deposited at 30 nm instead of 25 nm, A light emitting device was fabricated.
[평가예 2][Evaluation Example 2]
실시예 14 내지 24 및 비교예 2에서 각각 제조된 유기 전계 발광 소자에 대하여, 전류밀도 10 mA/㎠에서의 구동전압, 발광파장, 전류효율, 발광파장을 측정하였고, 그 결과를 하기 표 2에 나타내었다.The driving voltage, the emission wavelength, the current efficiency and the emission wavelength at the current density of 10 mA / cm 2 were measured for the organic electroluminescent devices manufactured in Examples 14 to 24 and Comparative Example 2, Respectively.
| 샘플Sample | 전자수송보조층Electron transporting auxiliary layer | 구동 전압(V)The driving voltage (V) | 발광 피크(nm)Emission peak (nm) | 전류효율cd/A)Current efficiency cd / A) |
| 실시예 14Example 14 | 화합물 5Compound 5 | 3.53.5 | 450450 | 8.58.5 |
| 실시예 15Example 15 | 화합물 18Compound 18 | 3.63.6 | 450450 | 8.88.8 |
| 실시예 16Example 16 | 화합물 40Compound 40 | 3.33.3 | 452452 | 8.68.6 |
| 실시예 17Example 17 | 화합물 53Compound 53 | 3.83.8 | 451451 | 9.09.0 |
| 실시예 18Example 18 | 화합물 65Compound 65 | 3.63.6 | 450450 | 9.29.2 |
| 실시예 19Example 19 | 화합물 84Compound 84 | 4.04.0 | 450450 | 8.58.5 |
| 실시예 20Example 20 | 화합물 90Compound 90 | 3.83.8 | 452452 | 8.48.4 |
| 실시예 21Example 21 | 화합물 113Compound 113 | 3.43.4 | 452452 | 8.98.9 |
| 실시예 22Example 22 | 화합물 122Compound 122 | 3.33.3 | 451451 | 8.68.6 |
| 실시예 23Example 23 | 화합물 133Compound 133 | 3.73.7 | 452452 | 8.28.2 |
| 실시예 24Example 24 | 화합물 165Compound 165 | 3.93.9 | 450450 | 8.88.8 |
| 비교예 2Comparative Example 2 | -- | 4.84.8 | 457457 | 5.85.8 |
표 2에 나타낸 바와 같이, 본 발명에 따른 화합물로 형성된 전자수송보조층을 포함하는 실시예 14 내지 24의 청색 유기 전계 발광 소자는 전자수송보조층 없이 Alq3로 된 전자수송층을 포함하는 비교예 2의 유기 전계 발광 소자에 비해 전류 효율 및 구동전압 면에서 우수한 성능을 나타내는 것을 알 수 있었다.As shown in Table 2, the blue organic electroluminescent devices of Examples 14 to 24 including the electron transporting auxiliary layer formed of the compound according to the present invention had the electron transporting layer of Alq 3 without the electron transporting auxiliary layer, The organic EL device of the present invention exhibits excellent current efficiency and excellent driving voltage.
Claims (14)
- 하기 화학식 1로 표시되는 화합물:A compound represented by the following formula (1):[화학식 1][Chemical Formula 1]
상기 화학식 1에서,In Formula 1,n은 1 내지 3의 정수이고;n is an integer from 1 to 3;Z1 내지 Z3은 각각 독립적으로 N 또는 C(R3)이고, 반드시 하나는 N이며;Z 1 to Z 3 are each independently N or C (R 3 ), and one is necessarily N;L1 및 L3는 각각 독립적으로 단일결합, C6~C18의 아릴렌기 및 핵원자수 5 내지 18개의 헤테로아릴렌기로 이루어진 군에서 선택되고; L 1 and L 3 are each independently selected from the group consisting of a single bond, a C 6 to C 18 arylene group and a heteroarylene group having 5 to 18 nucleus atoms;L2는 C6~C18의 아릴렌기 또는 핵원자수 5 내지 18개의 헤테로아릴렌기이며;L 2 is an arylene group having 6 to 18 carbon atoms or a heteroarylene group having 5 to 18 nuclear atoms;R1 내지 R3은 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되고, 상기 R3이 복수 개인 경우 이들은 서로 동일하거나 상이하며; R 1 to R 3 are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ of C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 6 ~ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C 1 ~ alkyloxy group of C 40, C 6 ~ aryloxy group of C 60, C 3 ~ C 40 alkylsilyl group, C group 6 ~ C 60 aryl silyl, C 1 ~ arylboronic of C 40 group of an alkyl boron, C 6 ~ C 60 group, C 6 ~ C 60 aryl phosphazene group, is selected from the group consisting of an aryl amine of the C 6 ~ C 60 mono or diaryl phosphine blood group and a C 6 ~ C 60 of, in the case where the R 3 a plurality individual which the same or different, and ;Ar1 및 Ar2는 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되고;Ar 1 and Ar 2 are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ of C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 6 ~ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C 1 ~ alkyloxy group of C 40, C 6 ~ aryloxy group of C 60, C 3 ~ C 40 alkylsilyl group, C group 6 ~ C 60 aryl silyl, C 1 ~ arylboronic of C 40 group of an alkyl boron, C 6 ~ C 60 group, C 6 ~ C 60 aryl phosphazene group, C 6 ~ C 60 mono or diaryl phosphine blood group and a C 6 ~ C 60 is selected from the group consisting of an aryl amine;상기 L1 내지 L3의 아릴렌기 및 헤테로아릴렌기와, 상기 Ar1, Ar2 및 R1 내지 R3의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이하다.Wherein Ar 1 , Ar 2, and Ar 3, which are the above-mentioned L 1 to L 3 arylene group and heteroarylene group, The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkylboron group, arylboron group of R 1 to R 3 A halogen atom, a cyano group, a nitro group, a C 1 to C 40 alkyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkenyl group, a substituted or unsubstituted aryl group, ~ C 40 of the alkynyl group, C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 6 ~ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C 1 ~ alkyloxy of C 40, C 6 ~ C 60 of the aryloxy group, an alkyl boronic of C 3 ~ C 40 alkylsilyl group, a group C 6 ~ C 60 aryl silyl, C 1 ~ C 40 group, C 6 ~ for C 60 aryl boron group, C 6 ~ C 60 aryl phosphazene group, one member selected from the group consisting of C 6 ~ C 60 mono or diaryl phosphine of blood group and a C 6 ~ C 60 aryl amine of the And when they are substituted with a plurality of substituents, they are the same as or different from each other. - 제1항에 있어서,The method according to claim 1,상기 화합물은 하기 화학식 2 내지 4 중 어느 하나로 표시되는 화합물:Wherein said compound is represented by any one of the following formulas (2) to (4):[화학식 2](2)
[화학식 3](3)
[화학식 4][Chemical Formula 4]
상기 화학식 2 내지 4에서,In the above Chemical Formulas 2 to 4,L1 내지 L3, Z1 내지 Z3, R1, R2, Ar1 및 Ar2 각각은 제1항에서 정의된 바와 같다.L 1 to L 3, Z 1 to Z 3, R 1, R 2 , Ar < 1 > and Ar < 2 > are as defined in claim 1, - 제1항에 있어서,The method according to claim 1,상기 화합물은 하기 화학식 5로 표시되는 화합물:The compound is a compound represented by the following formula (5): < EMI ID =[화학식 5][Chemical Formula 5]
상기 화학식 5에서,In Formula 5,n, L1 내지 L3, R1, R2, Ar1 및 Ar2 각각은 제1항에서 정의된 바와 같다.n, L 1 to L 3, R 1, R 2 , Ar < 1 > and Ar < 2 > are as defined in claim 1, - 제1항에 있어서,The method according to claim 1,상기 R1 내지 R3은 각각 독립적으로 C1~C40의 알킬기, C6~C60의 아릴기 및 핵원자수 5 내지 60개의 헤테로아릴기로 이루어진 군에서 선택되고,Each of R 1 to R 3 is independently selected from the group consisting of a C 1 to C 40 alkyl group, a C 6 to C 60 aryl group, and a heteroaryl group having 5 to 60 nuclear atoms,상기 R1 내지 R3의 알킬기, 아릴기 및 헤테로아릴기는 각각 독립적으로 C1~C40의 알킬기, C6~C60의 아릴기 및 핵원자수 5 내지 60개의 헤테로아릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이한 화합물.The alkyl, aryl and heteroaryl groups of R 1 to R 3 are each independently selected from the group consisting of a C 1 to C 40 alkyl group, a C 6 to C 60 aryl group, and a heteroaryl group having 5 to 60 nuclear atoms. And when they are substituted with a plurality of substituents, they are the same as or different from each other.
- 제1항에 있어서,The method according to claim 1,상기 L1 및 L3는 각각 독립적으로 단일결합, 페닐렌기, 비페닐렌기, 피리디닐기, 피리미디닐기, 나프탈레닐기, 플루오레닐기, 카바졸릴기, 디벤조퓨라닐기 및 디벤조티오페닐렌기로 이루어진 군에서 선택되고; Each of L 1 and L 3 independently represents a single bond, a phenylene group, a biphenylene group, a pyridinyl group, a pyrimidinyl group, a naphthalenyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, ≪ / RTI >상기 L2는 페닐렌기, 비페닐렌기, 피리디닐기, 피리미디닐기, 나프탈레닐기, 플루오레닐기, 카바졸릴기, 디벤조퓨라닐기 및 디벤조티오페닐렌기로 이루어진 군에서 선택되며; L 2 is selected from the group consisting of phenylene, biphenylene, pyridinyl, pyrimidinyl, naphthalenyl, fluorenyl, carbazolyl, dibenzofuranyl and dibenzothiophenylene;상기 L1 내지 L3의 페닐렌기, 비페닐렌기, 피리디닐기, 피리미디닐기, 나프탈레닐기, 플루오레닐기, 카바졸릴기, 디벤조퓨라닐기 및 디벤조티오페닐렌기는 각각 독립적으로 C1~C40의 알킬기, C6~C60의 아릴기 및 핵원자수 5 내지 60개의 헤테로아릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이한 화합물.The phenylene group, biphenylene group, pyridinyl group, pyrimidinyl group, naphthalenyl group, fluorenyl group, carbazolyl group, dibenzofuranyl group and dibenzothiophenylene group of L 1 to L 3 are each independently C 1 ~ C 40 alkyl group, substituted with one substituent at least one selected from the group consisting of C 6 ~ C 60 aryl group and the number of nuclear atoms of 5 to 60 heteroaryl group, or is unsubstituted, in the case where the substitution of a plurality of substituents, these are together Same or different compounds.
- 제1항에 있어서,The method according to claim 1,상기 L1 및 L3는 각각 독립적으로 단일결합이거나, 하기 화학식 A-1 내지 A-4로 이루어진 군에서 선택된 링커인 화합물:Wherein L 1 and L 3 are each independently a single bond or a linker selected from the group consisting of the following formulas A-1 to A-4:
상기 화학식 A-1 내지 A-4에서,In the above Formulas A-1 to A-4,*는 결합이 이루어지는 부분을 의미한다.* Means the part where the combination is made. - 제6항에 있어서,The method according to claim 6,상기 A-1로 표시되는 링커는 하기 화학식 B-1 또는 B-2로 표시되는 링커인 화합물:Wherein the linker represented by A-1 is a linker represented by the following formula (B-1) or (B-2):
상기 화학식 B-1 및 B-2에서,In the above Formulas B-1 and B-2,*는 결합이 이루어지는 부분을 의미한다.* Means the part where the combination is made. - 제1항에 있어서,The method according to claim 1,상기 L2는 하기 화학식 A-3 또는 A-4로 표시되는 링커인 화합물:Wherein L < 2 > is a linker represented by the following formula (A-3) or (A-
상기 화학식 A-3 및 A-4에서,In the above Formulas A-3 and A-4,*는 결합이 이루어지는 부분을 의미한다.* Means the part where the combination is made. - 제1항에 있어서,The method according to claim 1,상기 L2는 하기 화학식 C-1 내지 C-4로 이루어진 군에서 선택된 링커인 화합물:Wherein L < 2 > is a linker selected from the group consisting of the following formulas C-1 to C-4:
상기 화학식 C-1 내지 C-4에서,In the above formulas C-1 to C-4,*는 결합이 이루어지는 부분을 의미한다.* Means the part where the combination is made. - 제1항에 있어서,The method according to claim 1,상기 Ar1 및 Ar2는 각각 독립적으로 C1~C40의 알킬기, C6~C60의 아릴기 및 핵원자수 5 내지 60개의 헤테로아릴기로 이루어진 군에서 선택되고,Each of Ar 1 and Ar 2 is independently selected from the group consisting of a C 1 to C 40 alkyl group, a C 6 to C 60 aryl group, and a heteroaryl group having 5 to 60 nuclear atoms,상기 Ar1 및 Ar2의 알킬기, 아릴기 및 헤테로아릴기는 각각 독립적으로 C1~C40의 알킬기, C6~C60의 아릴기 및 핵원자수 5 내지 60개의 헤테로아릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이한 화합물. The alkyl, aryl and heteroaryl groups of Ar 1 and Ar 2 are each independently selected from the group consisting of a C 1 to C 40 alkyl group, a C 6 to C 60 aryl group, and a heteroaryl group having 5 to 60 nuclear atoms. And when they are substituted with a plurality of substituents, they are the same as or different from each other.
- 제1항에 있어서,The method according to claim 1,상기 Ar1 및 Ar2는 각각 독립적으로 하기 화학식 D-1 내지 D-7 중 어느 하나로 표시되는 치환기인 화합물:Wherein Ar 1 and Ar 2 are each independently a substituent represented by any one of the following formulas D-1 to D-7:
상기 화학식 D-1 내지 D-7에서,In the above formulas D-1 to D-7,*은 결합이 이루어지는 부분을 의미하고;* Denotes the part where the bond is made;p는 0 내지 5의 정수이며;p is an integer from 0 to 5;q는 0 내지 4의 정수이며;q is an integer from 0 to 4;R4는 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴아민기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성하고, 상기 R4 가 복수 개인 경우 이들은 서로 동일하거나 상이하며;R 4 is hydrogen, deuterium, a halogen, a cyano group, a nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 6 ~ C 60 of the aryl group, nuclear atoms of 5 to 60 heteroaryl group, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkyloxy group of, C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group , C 6 to C 60 arylamine groups, C 1 to C 40 alkylsilyl groups, C 1 to C 40 alkylboron groups, C 6 to C 60 arylboron groups, C 6 to C 60 arylphospha group, C 6 ~ C 60 mono or diaryl the Phosphinicosuccinic selected from the group the group consisting of C 6 ~ with an aryl silyl group of C 60 or, by combining groups of neighboring case form a condensed ring, and individual said R 4 is a plurality, they Are the same or different from each other;상기 R4의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이하다.Alkyl groups of the R 4, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group, A halogen atom, a cyano group, a nitro group, a C 1 to C 40 alkyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, A C 6 to C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 6 to C 60 aryloxy group, a C 1 to C 40 alkyloxy group, a C 6 to C 60 C 3 to C 40 cycloalkyl groups, 3 to 40 nucleus atom heterocycloalkyl groups, C 1 to C 40 alkylsilyl groups, C 1 to C 40 alkylboron groups, C 6 to C 60 the arylboronic group, one member selected from the group consisting of C 6 ~ C 60 aryl phosphazene group, C 6 ~ C 60 mono or diaryl phosphine of blood group and a C 6 ~ C 60 aryl group in the silyl Substituted with a substituent being unsubstituted or, if substituted by a plurality of substituents, they are same as or different from each other. - 제1항에 있어서,The method according to claim 1,상기 화합물은 아래의 화합물로 이루어진 군에서 선택되는 것을 특징으로 하는 화합물: Wherein said compound is selected from the group consisting of:
- (i) 양극, (ii) 음극, 및 (iii) 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하는 유기 전계 발광 소자로서, 1. An organic electroluminescent device comprising: (i) an anode, (ii) a cathode, and (iii) one or more organic layers sandwiched between the anode and the cathode,상기 1층 이상의 유기물층 중에서 적어도 하나는 제1항의 화학식 1로 표시되는 화합물을 포함하는 것을 특징으로 하는 유기 전계 발광 소자.Wherein at least one of the one or more organic layers includes a compound represented by the general formula (1).
- 제13항에 있어서,14. The method of claim 13,상기 유기물층은 정공 주입층, 정공 수송층, 정공 수송 보조층, 전자 수송층, 전자 수송 보조층 및 발광층으로 이루어진 군에서 선택되는 하나 이상의 층을 포함하는, 유기 전계 발광 소자.Wherein the organic material layer comprises at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, a hole transporting auxiliary layer, an electron transporting layer, an electron transporting auxiliary layer and a light emitting layer.
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Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009203203A (en) * | 2008-02-29 | 2009-09-10 | Toyo Ink Mfg Co Ltd | Anthracene derivative and use thereof |
| KR101129241B1 (en) * | 2011-07-13 | 2012-03-22 | 덕산하이메탈(주) | Novel compound for organic electronic element, organic electronic element using the same, and terminal thereof |
| KR20120051598A (en) * | 2010-11-12 | 2012-05-22 | 주식회사 엘지화학 | New compounds and organic electronic device using the same |
| WO2013154064A1 (en) * | 2012-04-09 | 2013-10-17 | 国立大学法人九州大学 | Organic light emitting element, and light emitting material and compound used in same |
| KR20160027940A (en) * | 2014-09-02 | 2016-03-10 | 주식회사 엘지화학 | Organic light emitting device |
| KR20180046152A (en) * | 2016-10-27 | 2018-05-08 | 주식회사 두산 | Organic compounds and organic electro luminescence device comprising the same |
-
2017
- 2017-12-15 KR KR1020170172781A patent/KR102508485B1/en active IP Right Grant
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2018
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Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009203203A (en) * | 2008-02-29 | 2009-09-10 | Toyo Ink Mfg Co Ltd | Anthracene derivative and use thereof |
| KR20120051598A (en) * | 2010-11-12 | 2012-05-22 | 주식회사 엘지화학 | New compounds and organic electronic device using the same |
| KR101129241B1 (en) * | 2011-07-13 | 2012-03-22 | 덕산하이메탈(주) | Novel compound for organic electronic element, organic electronic element using the same, and terminal thereof |
| WO2013154064A1 (en) * | 2012-04-09 | 2013-10-17 | 国立大学法人九州大学 | Organic light emitting element, and light emitting material and compound used in same |
| KR20160027940A (en) * | 2014-09-02 | 2016-03-10 | 주식회사 엘지화학 | Organic light emitting device |
| KR20180046152A (en) * | 2016-10-27 | 2018-05-08 | 주식회사 두산 | Organic compounds and organic electro luminescence device comprising the same |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110452689A (en) * | 2019-08-22 | 2019-11-15 | 武汉尚赛光电科技有限公司 | A kind of electroluminescent organic material and organic electroluminescence device based on Triazolopyridine |
| CN110452689B (en) * | 2019-08-22 | 2023-02-28 | 武汉尚赛光电科技有限公司 | Triazolopyridine-based organic electroluminescent material and organic electroluminescent device |
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